HCID 86628913, compound → HCID 25225547, compound

HRID 1919444Notes

Reaction equation

HRID 1919444 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:39])([CH3:38])[C@@H:14]([O:30]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[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]([CH3:39])([CH3:38])[C@@H:14]([OH:30])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86628913HCID 86628913, compound

Product 1

HCID 25225547HCID 25225547, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (cyclohexyloxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (43c) (0.19 g, 0.34 mmol) and 0.13 g of 10 wt.-% of palladium on activated carbon in 10 mL of methanol (MeOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 0.13 g (80% yield) of the title compound (43) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.89-0.90 (2s, 3H), 0.93-0.94 (2s, 3H), 1.31-1.47 (br. m, 9H), 1.60-1.68 (br. m, 2H), 1.78-1.83 (br. m, 7H), 3.10-3.15 (m, 2H), 3.28-3.35 (m, 2H), 3.89-3.92 (m, 2H), 4.05-4.08 (2d, J=9.2, 9.6 Hz, 1H), 4.52-4.58 (m, 1H), 5.78-5.85 (2d, J=5.6, 5.6 Hz, 1H), 6.66-6.72 (m, 1H), 7.89-7.92 (br. m, 1H) ppm. MS (ESI) m/z: 482.07 (M+H)+, 503.83 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-62c12aeda7d042808ff3cbaaf1e06ee8
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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