Hydrochloric Acid → HCID 25225744, compound

HRID 1919441Notes

Reaction equation

HRID 1919441 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:36])([CH3:35])[C@@H:14]([O:27]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])=[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])([CH3:36])[C@@H:14]([OH:27])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([O:23][CH:24]([CH3:25])[CH3:26])=[O:22])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86628910HCID 86628910, compound

Product 1

HCID 25225744HCID 25225744, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (methylethoxycarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (40c) (13.0 g, 24.4 mmol), 3.2 g of 10 wt.-% of palladium on activated carbon in 40 mL of methanol (MeOH), and 0.2 mL of one molar (1.0 M) hydrochloric acid (HCl) was stirred overnight under a hydrogen atmosphere. Upon the completion of reaction and following aqueous work-up, 10.0 g (93% yield) of the title compound (40) was obtained as a colorless, viscous oil. RT=12.46 min and 14.22 min. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.89-0.91 (2s, 3H), 0.93-0.95 (2s, 3H), 1.21-1.24 (m, 6H), 1.45-1.47 (2d, J=5.2, 5.2 Hz, 3H), 1.78-1.83 (m, 5H), 3.10-3.15 (m, 2H), 3.30-3.33 (m, 2H), 3.89-3.93 (m, 2H), 4.05-4.08 (2d, J=9.2, 9.6 Hz, 1H), 4.73-4.82 (m, 1H), 5.78-5.85 (2d, J=6.0, 6.0 Hz, 1H), 6.65-6.71 (m, 1H), 7.89-7.92 (br. m, 1H) ppm. MS (ESI) m/z: 442.08 (M+H)+, 464.02 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customUpon the completion of reaction

Sources & evidence

ORD record
ord-f474c2babd99493db4dacfcc4b901a01
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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