Methanol → HCID 22873502, compound

HRID 1683664Notes

Reaction equation

HRID 1683664 reaction equation
[P:1]([O:19][CH2:20][C:21](=[O:46])[C@@H:22]([NH:30][C:31](=[O:45])[C@H:32]([CH2:41][CH:42]([CH3:44])[CH3:43])[NH:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([O:11]CC1C=CC=CC=1)([O:3]CC1C=CC=CC=1)=[O:2].CO>C(OCC)(=O)C.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[P:1]([O:19][CH2:20][C:21](=[O:46])[C@@H:22]([NH:30][C:31](=[O:45])[C@H:32]([CH2:41][CH:42]([CH3:43])[CH3:44])[NH:33][C:34]([O:36][C:37]([CH3:38])([CH3:40])[CH3:39])=[O:35])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([OH:3])([OH:11])=[O:2]

Participants

6

Reactant 2

HCID 887MethanolHCID 57140133HCID 57140133, compound

Product 1

HCID 22873502HCID 22873502, compoundYield 36.8%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 30 mg of 20% Pd(OH)2 in a solution of dibenzyl (3S)-[3-[(N-t-Butoxycarbonyl-L-leucyl)amino]-2-oxo-4-phenylbutyl] phosphate (30 mg, 0.046 mmol) in 1.0 mL of ethyl acetate was stirred under H2 (1 atm) at room temperature for 4 hours. The catalyst was filtered through Celite™ and the filtrate was concentrated to give the crude product. Flash chromatography (10% MeOH in CH2Cl2) gave 8 mg of pure product. MS: 471 m/z (M-1).

Workup

  1. filtrationThe catalyst was filtered through Celite™
  2. concentrationthe filtrate was concentrated
  3. customto give the crude product

Sources & evidence

ORD record
ord-f11f4d0bf2864bec961f7700a22af8ad
Source dataset
uspto-grants-1997_06
Patent number
US05639732

Reaction notes

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