Hydrochloric Acid → HCID 25225743, compound

HRID 1919425Notes

Reaction equation

HRID 1919425 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:25])[CH:22]([CH3:24])[CH3:23])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2].Cl>[Pd].CO>[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]([OH:26])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21](=[O:25])[CH:22]([CH3:23])[CH3:24])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86628898HCID 86628898, compound

Product 1

HCID 25225743HCID 25225743, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (2-methylpropanoyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (29c) (4.0 g, 9.4 mmol), 1.0 g of 10 wt.-% of palladium on activated carbon in 20 mL of methanol (MeOH) and 0.15 mL of one molar (1.0 M) hydrochloric acid (HCl) was stirred overnight under a hydrogen atmosphere. Upon completion of reaction and following aqueous work-up, 3.4 g (85% yield) of the title compound (29) was obtained as a colorless, viscous oil. RT=13.59 min and 18.45 min (by LC/UV). 1H NMR (400 MHz, CDCl3, both diastereomers): δ=0.95-0.99 (2s, 3H), 1.12-1.14 (2s, 3H), 1.17-1.20 (m, 6H), 1.55-1.57 (2d, J=5.6, 5.6 Hz, 3H), 1.99-2.00 (2s, 3H), 2.04-2.12 (m, 2H), 2.53-2.62 (m, 1H), 3.13-3.23 (m, 2H), 3.26-3.29 (br. m, 1H), 3.34-3.45 (m, 2H), 3.91-3.97 (2d, J=9.6, 9.2 Hz, 1H), 4.03-4.06 (m, 1H), 4.14-4.19 (2d, J=9.2, 9.2 Hz, 1H), 5.96-6.01 (br. m, 1H), 6.91-6.97 (m, 1H) ppm. MS (ESI) m/z: 426.04 (M+H)+, 447.99 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customUpon completion of reaction

Sources & evidence

ORD record
ord-fffad9887b87427b8a9a461742fa3fb3
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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