(methylethoxycarbonyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate → HCID 86628891, compound

HRID 1919419Notes

Reaction equation

HRID 1919419 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][O:19][C:20]([O:22][CH:23]([CH3:25])[CH3:24])=[O:21])=[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]([CH3:34])([CH3:35])[C@@H:14]([OH:26])[C:15]([O:17][CH2:18][O:19][C:20]([O:22][CH:23]([CH3:24])[CH3:25])=[O:21])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86628892(methylethoxycarbonyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate

Product 1

HCID 86628891HCID 86628891, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure of hydrogenolysis of benzyl ethers of Description 18, a mixture of (methylethoxycarbonyloxy)methyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (27c) (16 mg, 0.03 mmol) and 20 mg of 10 wt.-% of palladium on activated carbon in 2 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 11 mg (83% yield) of the title compound (27) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=1.01 (s, 3H), 1.13 (s, 3H), 1.33-1.35 (m, 6H), 2.00 (s, 3H), 2.07-2.11 (m, 2H), 3.13-3.26 (m, 2H), 3.35-3.45 (m, 2H), 3.97 (d, J=9.2 Hz, 1H), 4.12 (s, 1H), 4.16 (d, J=9.6 Hz, 1H), 4.94 (sept., J=6.4 Hz, 1H), 5.79 (d, J=5.6 Hz, 1H), 5.81-5.89 (br. m, 1H), 5.91 (d, J=5.6 Hz, 1H), ppm. MS (ESI) m/z: 428.04 (M+H)+, 450.02 (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-17fba856fc0d4721a6bce082536c57e9
Source dataset
uspto-grants-2012_05
Patent number
US08168617B2

Reaction notes

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