Hydrochloric Acid → HCID 25225740, compound

HRID 1919447Notes

Reaction equation

HRID 1919447 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:38])([CH3:37])[C@@H:14]([O:29]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[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]([CH3:38])([CH3:37])[C@@H:14]([OH:29])[C:15]([O:17][CH2:18][CH2:19][O:20][C:21]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:22])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86628916HCID 86628916, compound

Product 1

HCID 25225740HCID 25225740, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of (cyclohexylcarbonyloxy)ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (44c) (0.79 g, 1.4 mmol), 0.4 g of 10 wt.-% of palladium on activated carbon in 20 mL of methanol (MeOH), and 30 μL of one molar (1.0 M) of hydrochloric acid (HCl) was stirred overnight under a hydrogen atmosphere. Upon the completion of reaction and following aqueous work-up, 0.62 g (94% yield) of the title compound (44) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, DMSO-d6, both diastereomers): δ=0.92-0.94 (2s, 3H), 0.97-0.98 (2s, 3H), 1.20-1.42 (br. m, 5H), 1.46-1.48 (2d, J=5.6, 5.6 Hz, 3H), 1.55-1.62 (br. m, 1H), 1.66-1.70 (br. m, 2H), 1.80-1.87 (m, 7H), 2.33-2.40 (m, 1H), 3.14-3.19 (m, 2H), 3.34-3.37 (m, 2H), 3.92-3.96 (m, 2H), 4.09-4.12 (2d, J=9.2, 9.6 Hz, 1H), 5.50-6.87 (2d, J=5.2, 5.6 Hz, 1H), 6.81-6.87 (m, 1H), 7.95-7.98 (br. m, 1H) ppm. MS (ESI) m/z: 466.10 (M+H)+, 488.07 (M+Na)+. The analytical data was consistent with the proposed structure.

Workup

  1. customUpon the completion of reaction

Sources & evidence

ORD record
ord-3f0254ce59f645c38eb54576489f1d71
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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