Hydrochloric Acid → HCID 59385221, compound

HRID 2356831Notes

Reaction equation

HRID 2356831 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)[CH:6]=[CH:7][C:8]=1[C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10].Cl>C(O)C.[Fe]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:5]2[CH:6]=[CH:7][C:8]([C:9]([NH:11][C@H:12]([C:16]([O:18][CH3:19])=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385317HCID 59385317, compound

Product 1

HCID 59385221HCID 59385221, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Iron powder (0.35 g, 6.2 mmol) was added to a solution of methyl N-[(3-methoxy-4′-nitrobiphenyl-4-yl)carbonyl]-L-valinate (0.30 g, 0.62 mmol) in ethanol (10 mL). Concentrated HCl (0.31 mL, 0.62 mmol) was added, and the mixture was heated at reflux for 1 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 0.296 g (quantitative) of the title compound. LC/MS m/z 357.2 (MI), retention time 2.34 min.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1 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-b9641c501aa5402292be598f061c76a8
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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