Hydrochloric Acid → methyl N-[(4'-amino-3-chlorobiphenyl-4-yl)carbonyl]-L-valinate

HRID 2356834Notes

Reaction equation

HRID 2356834 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH:5]=[CH:6][C:7]=1[C:8]([NH:10][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]([CH3:14])[CH3:13])=[O:9].Cl>C(O)C.[Fe]>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:4]2[CH:5]=[CH:6][C:7]([C:8]([NH:10][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH:12]([CH3:13])[CH3:14])=[O:9])=[C:2]([Cl:1])[CH:3]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385306methyl N-[(3-chloro-4'-nitrobiphenyl-4-yl)carbonyl]-L-valinate

Product 1

HCID 59385210methyl N-[(4'-amino-3-chlorobiphenyl-4-yl)carbonyl]-L-valinateYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.44 g, 7.8 mmol) was added to a solution of methyl N-[(3-chloro-4′-nitrobiphenyl-4-yl)carbonyl]-L-valinate (0.30 g, 0.78 mmol) in ethanol (10 mL). Concentrated HCl (0.39 mL, 0.78 mmol) was added, and the mixture was heated at reflux for 3 h. Upon cooling to rt, the mixture was filtered through a pad of Celite®, and the filtrate was concentrated in vacuo. The material was purified by column chromatography (33% EtOAc in hexanes), yielding 0.25 g (89%) of the title compound. LC/MS m/z/z 361.2 (MH+), retention time 2.36 min. 1H NMR (400 MHz, CD2Cl2) δ 1.06 (dd, 6H), 2.32-2.39 (m, 1H), 3.80 (s, 3H), 4.71-4.78 (m, 1H), 6.82 (d, 3H), 7.40-7.74 (m, 5H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 3 h
  3. filtrationthe mixture was filtered through a pad of Celite®
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe material was purified by column chromatography (33% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ad7aad72ac0148d78dddaa13a17ac126
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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