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CAS No. : | 7292-74-2 | MDL No. : | MFCD00049325 |
Formula : | C8H8FNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | LVYBCZIDQKJNFP-UHFFFAOYSA-N |
M.W : | 169.15 | Pubchem ID : | 265434 |
Synonyms : |
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Chemical Name : | 2-Amino-2-(3-fluorophenyl)acetic acid |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-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 |
---|---|---|
69% | To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 1 1.8 mmol) were added and the reaction was stirred at RT for 15h. THF was evaporated, the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3- fluorophenyl)acetic acid (1.10 g; 69% yield). | |
69% | With sodium hydroxide; In tetrahydrofuran; water; at 20℃; for 15h; | To a suspension of <strong>[7292-74-2]2-amino-2-(3-fluorophenyl)acetic acid</strong> (1.00 g, 5.91 mmol) in THF (30 ml) and water (30 ml), were added 2N sodium hydroxide (29.6 ml, 59.1 mmol) and di-tert-butyl dicarbonate (2.58 g, 11.8 mmol), and the reaction was stirred at RT for 15 hours. THF was evaporated, and the aqueous phase was cooled and acidified with 37% HCl until pH 1. The desired compound was extracted with EtOAc, and the organic phase was washed with brine, dried over Na2SO4 and evaporated to obtain 2-(tert-butoxycarbonylamino)-2-(3-fluorophenyl)acetic acid (1.10 g; 69% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Substitution in the procedure of Example 3 for the N-tert.-butoxycarbonyl derivative of D-α-aminophenylacetic acid (also called D-α-tert.-butoxycarboxamidophenylacetic acid) of an equimolar weight of the N-tert.-butoxycarbonyl derivative of ... D-α-amino-m-methylphenylacetic acid, D-α-amino-p-chlorophenylacetic acid, D-α-amino-m-chlorophenylacetic acid, D-α-amino-p-fluorophenylacetic acid, D-α-amino-m-fluorophenylacetic acid, D-α-amino-p-aminophenylacetic acid, D-α-amino-p-dimethylaminophenylacetic acid, D-α-amino-m,p-dimethoxyphenylacetic acid, ... | ||
The hydantoin was hydrolyzed at reflux using 1 N NaOH giving 2-amino-2-(3-fluorophenyl)acetic acid which was esterified via Procedure H in methanol to give the title compound. |