(R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acid → (R)-2-(4-Amino-2-fluorobenzamido)propanoic acid

HRID 1399462Notes

Reaction equation

HRID 1399462 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 78976542(R)-2-(2-Fluoro-4-nitrobenzamido)propanoic acid

Product 1

HCID 86713131(R)-2-(4-Amino-2-fluorobenzamido)propanoic acidYield 72%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of iron powder (656 mg, 11.71 mmol) in AcOH (6 mL) was added (R)-2-(2-fluoro-4-nitrobenzamido)propanoic acid (300 mg, 1.17 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 white color solid (190 mg, 72%). 1H NMR (400 MHz, DMSO-d6): δ 7.68 (1H, br s, exchangeable with D2O), 7.56 (1H, t, J=9.0 Hz), 6.41 (1H, d, J=8.8 Hz), 6.31 (1H, d, J=15.2 Hz), 5.99 (2H, br s, exchangeable with D2O), 4.15 (1H, br s), 1.30 (3H, d, J=6.8 Hz); LC-MS (negative ion mode): m/z 225 (M−H)−.

Sources & evidence

ORD record
ord-9904c4b5aeac4d8ab4ca75c4fe7f5a05
Source dataset
uspto-grants-2014_12
Patent number
US08906344B2

Reaction notes

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