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CAS No. : | 2491-20-5 | MDL No. : | MFCD00063663 |
Formula : | C4H10ClNO2 | Boiling Point : | - |
Linear Structure Formula : | [CH3O2CCH(CH3)NH3]Cl | InChI Key : | IYUKFAFDFHZKPI-DFWYDOINSA-N |
M.W : | 139.58 | Pubchem ID : | 2733257 |
Synonyms : |
L-Alanine methyl ester (hydrochloride);Methyl L-Alaninate;L-Alanine methyl ester hydrochloride
|
Chemical Name : | H-Ala-OMe.HCl |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
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 |
---|---|---|
17.82 g | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; | To a solution of 4-hydroxyphenylglycine (12 g, 71.860 mmol) in a 1:1 mixture of acetone and water was addeddi-tert-butyldicarbonate (16.5 mL, 71.8 mmol, 1 eq) andsodium bicarbonate (6.03 g, 0.11 mol, 1.5 eq). The solutionwas allowed to stir overnight, and then was quenched with theaddition of citric acid (pH 3) to pH 4. The aqueous layer was65 then extracted 2x with EtOAc and the combined organiclayers were washed with brine, dried over Na2S04 and concentratedto a white foam. The crude material (18.43 g, 69mmol (assumed)) was used without further purification bydissolving it in anhydrous DMF and treating sequentiallywith triethylamine (12.6 mL, 75.9 mmol, 1.3 eq), HOBT(9.32 g, 69 mmol, 1 eq) andAla-OMe HCl (9.63 g, 69 mmol,1 eq). The solution was then cooled to oo C. and EDC (19.55 5g, 0.1 mol, 1.5 eq) was added in one portion. The reaction wasallowed to warm to room temperature and stirred overnight.Water and EtOAc were added, the aqueous layer wasextracted 3x, and the combined organic layers were washedwith brine, dried over Na2S04 and concentrated. The residue 10was purified by flash chromatography (6% MeOH, 0.6%AcOH in DCM) to give a clear residue (17.82 g, 71% yield).Rf=0.39 (7% MeOH in DCM). 1H NMR (CDC13 , 600 MHz)o (ppm) 7.11 (d, 1=8.4 Hz, 2H), 6.64 (d, 1=8.4 Hz, 2H), 6.51 15(brd, 1=6.6 Hz, lH), 5.71 (brs, lH), 5.07 (brs, lH), 4.57-4.52(m, 1H),3.69(s,3H), 1.42-1.40(m, 12H). 13CNMR(CDC13 ,600 MHz) o (ppm) 173.2, 170.5, 156.6, 155.4, 129.0, 128.7(2C), 116.1 (2C), 80.5, 58.2, 52.7, 48.5, 28.4 (3C), 18.4. IR(film)vmax=1655, 1512,1450,1365,1215,1157,1049 cm-1. 20ESI HRMS calcd for [(M+NatJ C17H24N20 6 : 375.1526.found: 375.1532. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.3 g | (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanamido)propanoate To a solution of <strong>[5545-54-0](S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(tert-butoxy)phenyl)propanoic acid</strong> (2.24 g, 6.03 mmol) and (S)-methyl 2-aminopropanoate hydrochloride (0.850 g, 6.09 mmol) in DCM (30.2 ml) at 0 C. was added solid HATU (2.408 g, 6.33 mmol). After 15 mins N-methylmorpholine (1.326 ml, 12.06 mmol) was added and the mixture was allowed to warm to RT, overnight. Added 1 N HCl 30 ml and extracted 3* with dichloromethane (30 mL), combined organics were dried over Na2SO4, filtered, and stripped to a wax. The residue was purified via normal phase chromatography, ISCO 80 grams silica, hexanes to ethyl acetate gradient, produced 1.3 grams. LCMS Condition E: retention time=0.97 mins 457.5 (M+1); 1H NMR (400 MHz, CHLOROFORM-d) delta 7.40-7.31 (m, 5H), 7.14-7.05 (m, J=8.1 Hz, 2H), 6.97-6.84 (m, 2H), 5.31 (s, 1H), 5.11 (s, 2H), 4.49 (s, 1H), 3.72 (s, 3H), 1.57 (br. s., 2H), 1.38-1.29 (m, 12H). |