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CAS No. : | 28875-17-4 | MDL No. : | MFCD00038513 |
Formula : | C9H17NO4 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | GJDICGOCZGRDFM-LURJTMIESA-N |
M.W : | 203.24 | Pubchem ID : | 10856577 |
Synonyms : |
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Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31%; 31.7% | With n-butyllithium; diisopropylamine; In tetrahydrofuran; at -78 - -40℃; for 5h; | To a solution of diisopropylamine (16.97 mL, 119 mmol) in THF (60 mL), butyllithium (74.4 mL, 119 mmol) was slowly added. The reaction was stirred at -78 C. for 1 hour, at which time a solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)propanoate (11 g, 54.1 mmol) in 40 mL THF was added. The reaction was allowed to stir for another 2 hours, at which time 5-methylisoxazole-3-carbaldehyde (7.82 g, 70.4 mmol) in 10 mL THF was added. The reaction was allowed to stir at -78 C. for another 2 hours and then warm -40 C. The reaction was quenched with saturated aqueous NH4Cl solution and was then allowed to warm to room temperature. The mixture was extracted with EtOAc. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The crude material was purified by silica gel column chromatography, (EtOAc/heptane, 0-30%) to afford (±)-3.1e (5.3 g, 31% yield) and (±)-3.1.e′ (5.4 g, 17.18 mmol, 31.7% yield). The less polar fraction is the desired diastereomers (±)-3.1e. (0531) (±)-3.1e: 1H NMR (400 MHz, CDCl3) 6.03-6.14 (m, 1H), 6.00 (s, 1H), 5.78-5.89 (m, 1H), 5.31 (d, J=9.5 Hz, 1H), 3.85 (s, 3H), 2.40 (d, J=0.6 Hz, 3H), 1.70 (s, 3H), 1.43 (s, 9H). LCMS (m/z): 315.3 [M+H]+. (0532) The diastereomer (±)-3.1e was separated by chiral SFC to afford two enantiomers: Isomer 1: tR 1.45 min and isomer 2: tR 2.76 min. The isomer 2 is the desired enantiomer 3.1e. (0533) SFC separation condition: (0534) Chiral AD column; flow rate 100 ml/min; CO2/EtOH=90/10; 293 bar. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With water; In aq. phosphate buffer; N,N-dimethyl-formamide; at 30℃; for 6h;pH 7.2; | General procedure: The soil samples were collected from various locations inChina, and then the strains were screened by utilizing N-Boc-2-aminobutyrate as a sole carbon source and selective platewith bromocresol purple indicator. Isolated strains weretransferred to 150 mL fermentation medium and cultivatedat 200 rpm, 30 C for 48 h. After the cells were harvested, 1 g wet cell were washed and suspended in 5 mL 0.1 M,pH 7.0 potassium phosphate buffer (KPB). Cell suspensionswere mixed with 50 muL substrate solution (N-Boc-2-aminobutyrate:acetone = 1:4,V/V) and kept at 200 rpm, 30 Cfor 6 h reaction, the enantioselective hydrolysis of the substratewas determined by GC-MS. The screening mediumcontained (per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O,1 g K2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,0.25 g Bromocresolpurple, 20 g agar. Fermentation medium contained(per liter, pH 7) 0.5 g KCl, 0.5 g MgSO47H2O, 1 gK2HPO43H2O, 3 g NaNO3,0.01 g FeSO4,20 g sucrose. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | Isobutyl chloroformate (15.66 g, 114.70 mmol) was added to a solution of methyl N-(tert-butoxycarbonyl)-l-alaninate (27.1 g, 143.37 mmol) and N-Methylmorpholine (11.6 g, 114.70 mmol) in THF (100 ml) at 0C and the reaction temperature was allowed to rise to 25 C and stirred for 1 hour. N-benzyl-D-serinate (20 g, 95.58 mmol) in THF (100 ml) was then added and the mixture was stirred overnight. The reaction mixture was filtered and washed with EtOAc. After removing the solvents under reduced pressure, the crude product was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in petroleum ether. Pure fractions were evaporated to dryness to afford methyl N-(ferf-butoxycarbonyl)-L-alanyl-N-benzyl-D-serinate (16 g, 44%) as a colourless oil. 1H NMR (400 MHz, CDCIs, 30C) 1.22 (3H, d), 1.44 (9H, s), 3.74 (3H, s), 3.91 (2H, d), 4.06 (1H, m), 4.53 - 4.63 (1H, m), 4.72 (1H, m), 4.84 (1H, m), 5.28 (1H, m), 7.31 - 7.45 (5H, m). One exchangeable proton not seen m/z: ES+ [M+H]+ = 381. |
[ 69942-12-7 ]
Methyl 2-((tert-butoxycarbonyl)amino)-3-hydroxypropanoate
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