HCID 61708911, compound → (S)-2-(4-amino-2-fluorobenzamido)propanoic acid

HRID 1399460Notes

Reaction equation

HRID 1399460 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[C:4]([NH:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[O:5]>CC(O)=O.[Fe]>[NH2:16][C:14]1[CH:13]=[CH:12][C:3]([C:4]([NH:6][C@@H:7]([CH3:11])[C:8]([OH:10])=[O:9])=[O:5])=[C:2]([F:1])[CH:15]=1

Participants

4

Reactant 1

HCID 61708911HCID 61708911, compound

Product 1

HCID 86713130(S)-2-(4-amino-2-fluorobenzamido)propanoic acidYield 75.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of iron powder (175 mg, 3.12 mmol) in AcOH (2 mL) was added (S)-2-(2-fluoro-4-nitrobenzamido)propanoic acid (80 mg, 0.31 mmol) at rt and stirred at 60-70° C. for 20 min. Work-up of the reaction mixture as described in example 6 gave the product as a pale brown color solid (53 mg, 75%), mp 244-248° C. 1H NMR (400 MHz, DMSO-d6): δ 7.69 (1H, br s), 7.55 (1H, t, J=8.8 Hz), 6.41 (1H, d, J=8.4 Hz), 6.30 (1H, d, J=14.8 Hz), 5.97 (2H, br s), 4.15 (1H, br s), 1.31 (3H, d, J=6.8 Hz); LC-MS (positive ion mode): m/z 227 (M+H)+.

Sources & evidence

ORD record
ord-c0ff6b13573841f896c9e9d50f9542cd
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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