isopropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate → HCID 25218129, compound
Reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:30])([CH3:29])[C@@H:14]([O:21]CC1C=CC=CC=1)[C:15]([O:17][CH:18]([CH3:20])[CH3:19])=[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]([CH3:29])([CH3:30])[C@@H:14]([OH:21])[C:15]([O:17][CH:18]([CH3:19])[CH3:20])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of isopropyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate (25c) (0.20 g, 0.45 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 after lyophilization of the solvents, 100 mg (63% yield) of the title compound (25) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.95 (s, 3H), 1.13 (s, 3H), 1.32 (d, J=6.0 Hz, 3H), 1.34 (d, J=6.4 Hz, 3H), 1.99 (s, 3H), 2.02-2.16 (m, 2H), 3.12-3.26 (m, 2H), 3.29 (br. d, J=6.0 Hz, 1H), 3.32-3.47 (m, 2H), 3.95 (d, J=9.6 Hz, 1H), 3.99 (br. d, J=4.8 Hz, 1H), 4.17 (d, J=9.2 Hz, 1H), 5.14 (septet, J=6.4 Hz, 1H), 6.00-6.06 (br. m, 1H) ppm. MS (ESI) m/z: 354.13 (M+H)+, 352.16 (M−H)−. The analytical data was consistent with the proposed structure.
Workup
- customAfter purification by mass-guided preparative HPLC after lyophilization of the solvents
Sources & evidence
- ORD record
- ord-8d268600044f48309294ac22bcb9c04a
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994218B2
Reaction notes
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