HCID 86629038, compound → HCID 25218253, compound

HRID 1671440Notes

Reaction equation

HRID 1671440 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:32])([CH3:31])[C@@H:14]([O:23]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[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]([CH3:31])([CH3:32])[C@@H:14]([OH:23])[C:15]([O:17][CH2:18][CH2:19][CH:20]([CH3:21])[CH3:22])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86629038HCID 86629038, compound

Product 1

HCID 25218253HCID 25218253, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of 3-methylbutyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (29c) (0.20 g, 0.42 mmol) and 200 mg of 10 wt-% of palladium on activated carbon in 10 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 160 mg (quant. yield) of the title compound (29) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.943 (d, J=6.8 Hz, 3H), 0.946 (d, J=6.8 Hz, 3H), 0.947 (s, 3H), 1.13 (s, 3H), 1.55-1.62 (m, 2H), 1.63-1.76 (m, 1H), 1.99 (s, 3H), 2.02-2.13 (m, 2H), 3.12-3.26 (m, 3H), 3.31-3.46 (m, 2H), 3.95 (d, J=9.6 Hz, 1H), 4.03 (s, 1H), 4.17 (d, J=9.2 Hz, 1H), 4.24 (t, J=6.8 Hz, 2H), 6.06-6.12 (br. m, 1H) ppm. MS (ESI) m/z: 382.00 (M+H)+, 380.04 (M−H)−. The analytical data was consistent with the proposed structure.

Workup

  1. customAfter purification by mass-guided preparative HPLC

Sources & evidence

ORD record
ord-8e37406ac37341af99de57a192ce5417
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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