HCID 131729678, compound → HCID 25225546, compound

HRID 1919438Notes

Reaction equation

HRID 1919438 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:38])([CH3:37])[CH:14]([O:29]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>[Pd].C(O)C>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:38])([CH3:37])[CH:14]([OH:29])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 131729678HCID 131729678, compound

Product 1

HCID 25225546HCID 25225546, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of benzoyloxyethyl (2R/S)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (39c) (1.7 g, 3.1 mmol) and 1.0 g of 10 wt.-% of palladium on activated carbon in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After work-up, the crude material was purified by silica gel column chromatography using a mixture of ethyl acetate (EtOAc) and methanol (MeOH) (EtOAc/MeOH=9:1) as eluent to provide 0.67 g (47% yield) of the title compound (39) as a colorless oil. The analytical data was consistent with the data obtained for benzoyloxyethyl (2R)-4-{[(3-acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (38).

Workup

  1. customAfter work-up, the crude material was purified by silica gel column chromatography
  2. additiona mixture of ethyl acetate (EtOAc) and methanol (MeOH) (EtOAc/MeOH=9:1) as eluent

Sources & evidence

ORD record
ord-1d051032f1984fcdb874e709223d4f3d
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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