Acetic Acid → HCID 54755652, compound

HRID 1919428Notes

Reaction equation

HRID 1919428 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:35])([CH3:34])[C@@H: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].C(O)(=O)C>[Pd].CO>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:34])([CH3:35])[C@@H: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

5

Reactant 2

HCID 176Acetic AcidHCID 86628902HCID 86628902, compound

Product 1

HCID 54755652HCID 54755652, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (ethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (32c) (5.2 g, 10 mmol), 1.3 g of 10 wt.-% of palladium on activated carbon in 20 mL of methanol (MeOH), and 1.0 mL (1.05 g, 17.5 mmol) of glacial acetic acid was stirred overnight under a hydrogen atmosphere. Upon the completion of reaction and following aqueous work-up, 3.6 g (84% yield) of the title compound (32) was obtained as a colorless, viscous oil. RT=21.95 min and 30.99 min (by LC/UV). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=0.99-1.01 (2s, 3H), 1.13-1.15 (2s, 3H), 1.32-1.37 (m, 3H), 1.59-1.62 (m, 3H), 2.00-2.01 (2s, 3H), 2.04-2.12 (m, 2H), 3.12-3.26 (m, 3H), 3.33-3.47 (m, 2H), 3.94-3.98 (m, 1H), 4.06-4.08 (2d, J=6.8, 6.0 Hz, 1H), 4.14-4.19 (2d, J=8.8, 8.8 Hz, 1H), 4.23-4.28 (m, 2H), 5.85-5.88 (br. m, 1H), 6.85 (m, 1H) ppm. MS (ESI) m/z: 428.14 (M+H)+, 450.14 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customUpon the completion of reaction

Sources & evidence

ORD record
ord-6c278b71f5fb45a898b7a173ced1d6d9
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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