HCID 131729675, compound → HCID 25225544, compound

HRID 1919434Notes

Reaction equation

HRID 1919434 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:35])([CH3:34])[CH:14]([O:26]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>[Pd].CO>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:34])([CH3:35])[CH:14]([OH:26])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 131729675HCID 131729675, compound

Product 1

HCID 25225544HCID 25225544, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of (ethoxycarbonyloxy)ethyl (2R/S)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (37c) (1.7 g, 3.3 mmol) and 1.4 g of 10 wt.-% of palladium on activated carbon in 30 mL of methanol (MeOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 500 mg (35% yield) of the title compound (37) was obtained as a yellow viscous oil after lyophilization of the solvents. The analytical data was consistent with the data obtained for (ethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-2-hydroxy-3,3-dimethylbutanoate (32).

Workup

  1. customAfter purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-b5ea35f6261548d8b7feea2cdeeecbd3
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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