HCID 86629041, compound → HCID 25218254, compound

HRID 1671443Notes

Reaction equation

HRID 1671443 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:31])([CH3:30])[C@@H:14]([O:22]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH:19]([CH3:21])[CH3:20])=[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]([CH3:30])([CH3:31])[C@@H:14]([OH:22])[C:15]([O:17][CH2:18][CH:19]([CH3:20])[CH3:21])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86629041HCID 86629041, compound

Product 1

HCID 25218254HCID 25218254, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of 2-methylpropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (30c) (0.43 g, 0.94 mmol) and 400 mg of 10 wt-% palladium on activated carbon in 10 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC and lyophilization of the solvents, 200 mg (58% yield) of the title compound (30) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.96-1.00 (m, 9H), 1.16 (s, 3H), 1.96-2.05 (m, 4H), 2.05-2.14 (m, 2H), 3.13-3.26 (m, 2H), 3.27 (d, J=6.4 Hz, 1H), 3.33-3.49 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 3.98 (d, J=6.4 Hz, 1H), 3.99-4.03 (m, 1H), 4.03-4.07 (m, 1H), 4.18 (d, J=8.8 Hz, 1H), 5.88-5.94 (br. m, 1H) ppm. MS (ESI) m/z: 368.16 (M+H)+, 366.19 (M−H)−. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter purification by mass-guided preparative HPLC and lyophilization of the solvents

Sources & evidence

ORD record
ord-3807960352294c1c9fb1f270ca1ebd4c
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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