HCID 19705442, compound → HCID 19705486, compound

HRID 727565Notes

Reaction equation

HRID 727565 reaction equation
C([O:8][NH:9][C:10](=[O:43])[CH:11]([CH2:30][CH2:31][NH:32][S:33]([C:36]1[CH:41]=[CH:40][C:39]([CH3:42])=[CH:38][CH:37]=1)(=[O:35])=[O:34])[C:12]1([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25])C1C=CC=CC=1>CO>[OH:8][NH:9][C:10](=[O:43])[CH:11]([CH2:30][CH2:31][NH:32][S:33]([C:36]1[CH:37]=[CH:38][C:39]([CH3:42])=[CH:40][CH:41]=1)(=[O:35])=[O:34])[C:12]1([CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]1=[O:25]

Participants

3

Reactant 1

HCID 19705442HCID 19705442, compound

Product 1

HCID 19705486HCID 19705486, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-benzyloxy-α-[2-[[(4-methylphenyl)sulfonyl]amino]ethyl]-3-(2-methylpropyl)-2-oxo-1-(2-phenylethyl)-3-pyrrolidineacetamide (133 mg, 0.220 mmol), MeOH (8.0 mL), and Pearlman's cat (25 mg) is hydrogenated (1 atm) for 8 h at room temperature. The mixture is filtered, the solids washed with MeOH (2×5 mL), CH2Cl2 (5 mL), and MeOH (5 mL). The combined filtrates are concentrated and the residue crystallized from EtOAc/hexane to give 84 mg (74%) of the title compound as a white solid (mp 166.5°-167° C.):

Workup

  1. customfor 8 h
  2. customat room temperature
  3. filtrationThe mixture is filtered
  4. washthe solids washed with MeOH (2×5 mL), CH2Cl2 (5 mL), and MeOH (5 mL)
  5. concentrationThe combined filtrates are concentrated
  6. customthe residue crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-e8ed557313ea4f4286209739d0836cb7
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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