HCID 86629023, compound → HCID 25218128, compound

HRID 1671429Notes

Reaction equation

HRID 1671429 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:28])([CH3:27])[C@@H:14]([O:19]CC1C=CC=CC=1)[C:15]([O:17][CH3:18])=[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]([CH3:28])([CH3:27])[C@@H:14]([OH:19])[C:15]([O:17][CH3:18])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86629023HCID 86629023, compound

Product 1

HCID 25218128HCID 25218128, compoundYield 39.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (24c) (0.45 g, 1.1 mmol) and 400 mg of 10 wt.-% of palladium on activated carbon in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 140 mg (39% yield) of the title compound (24) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.97 (s, 3H), 1.12 (s, 3H), 2.01 (s, 3H), 2.04-2.13 (m, 2H), 2.94-3.08 (br. s, 1H), 3.13-2.26 (m, 2H), 3.33-3.48 (m, 2H), 3.83 (s, 3H), 3.97 (d, J=8.8 Hz, 1H), 4.06 (br. s, 1H), 3.97 (d, J=9.6 Hz, 1H), 6.02-6.09 (br. m, 1H) ppm. MS (ESI) m/z: 325.95 (M+H)+, 323.97 (M−H)−. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-8fa063153316416cae54215187b473b8
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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