HCID 21187415, compound → HCID 21187427, compound

HRID 1383734Notes

Reaction equation

HRID 1383734 reaction equation
C(OC([NH:11][CH2:12][CH:13]([NH:26][C:27](=[O:53])[CH:28]([NH:32][CH2:33][CH:34]([NH:42]C(OCC1C=CC=CC=1)=O)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH:29]([CH3:31])[CH3:30])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:16]=1)=O)C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[NH2:42][CH:34]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:33][NH:32][CH:28]([CH:29]([CH3:30])[CH3:31])[C:27]([NH:26][CH:13]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[C:17]([C:22]([CH3:24])([CH3:25])[CH3:23])[CH:16]=1)[CH2:12][NH2:11])=[O:53]

Participants

5

Reactant 2

HCID 21187415HCID 21187415, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21187427HCID 21187427, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 132 mg (0.183 mmol) of N-[2-benzoxycarbonylamino-1-[(3-tert-butyl-4-hydroxyphenyl)methyl]ethyl]-2-[[2-(benzoxycarbonylamino)-3-phenylpropyl]amino]-3-methyl butanamide in methanol (2 ml), 10% palladium carbon (80 mg) was added and the mixture was stirred in a hydrogen atmosphere at room temperature for 2 days. After filtering, the filtrate was concentrated under reduced pressure and the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of chloroform, methanol and aqueous ammonia at a ratio of 10:1:0.1) to yield 2-[(2-amino-3-phenylpropyl)amino]-N-[2-amino-1-[(3-tert-butyl-4-hydroxyphenyl)methyl]ethyl]-3-methyl butanamide in the amount of 24.2 mg (29%).

Workup

  1. filtrationAfter filtering
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washeluting solvent

Sources & evidence

ORD record
ord-7b3eb4d5dcbf464fb4af1b2eb0d24646
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

Loading…