Hydrochloric Acid → HCID 67152104, compound

HRID 2356823Notes

Reaction equation

HRID 2356823 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH:23]([CH3:25])[CH3:24])[NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)=[O:7].Cl>C(O)C.[Fe]>[NH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:11]2[CH:12]=[CH:13][C:8]([C:6]([NH:5][C@H:4]([C:3]([O:2][CH3:1])=[O:26])[CH:23]([CH3:25])[CH3:24])=[O:7])=[CH:9][CH:10]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59385277HCID 59385277, compound

Product 1

HCID 67152104HCID 67152104, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl-N-[(4′-nitro-1,1′-biphenyl-4-yl)carbonyl]-L-valinate (0.70 g, 1.9 mmol) in 85% ethanol (20 mL) was added iron powder (1.09 g, 19.6 mmol) and 2N aqueous HCl solution (1.0 mL). The resulting mixture was heated at reflux for 2 h. The mixture was then filtered through a pad of Celite® and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with water and brine, dried (Na2SO4), and concentrated under reduced pressure to afford methyl N-[(4′-amino-1,1′-biphenyl-4-yl)carbonyl]-L-valinate (0.58 g, 90%). 1H NMR (400 MHz, CD3OD) δ 1.03 (dd, 6H), 2.26 (m, 1H), 3.74 (s, 3H), 4.48 (d, 1H), 6.77 (d, 2H), 7.43 (d, 2H), 7.62 (d, 2H), 7.83 (d, 2H); LC-MS m/z 327.1 (MH+), retention time 2.27 minutes.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationThe mixture was then filtered through a pad of Celite®
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washwashed with water and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e37ea9d2eaa94cc897f1e13cbb9731f0
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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