HCID 86629020, compound → HCID 25207673, compound

HRID 1671423Notes

Reaction equation

HRID 1671423 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:29])([CH3:28])[C@@H:14]([O:20]CC1C=CC=CC=1)[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:10])=[O:9])(=[O:3])[CH3:2]>C(O)C.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][S:8]([O:11][CH2:12][C:13]([CH3:28])([CH3:29])[C@@H:14]([OH:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:9])=[O:10])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86629020HCID 86629020, compound

Product 1

HCID 25207673HCID 25207673, compoundYield 62.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Following the general procedure for the hydrogenolysis of benzyl ethers of Description 18, a mixture of ethyl (2R)-4-{[3-(acetylamino)propyl]sulfonyloxy}-3,3-dimethyl-2-(phenylmethoxy)butanoate acid (22b) (0.8 g, 1.8 mmol) and 700 mg palladium (10 wt. % on activated carbon) in 20 mL of ethanol (EtOH) was stirred overnight under a hydrogen atmosphere. After purification by mass-guided preparative HPLC, 380 mg (61% yield) of the title compound (22) was obtained as a colorless, viscous oil. 1H NMR (400 MHz, CDCl3): δ=0.96 (s, 3H), 1.13 (s, 3H), 1.34 (t, J=7.2 Hz, 3H), 1.99 (s, 3H), 2.04-2.12 (m, 2H), 3.12-3.26 (m, 2H), 3.32 (d, J=6.0 Hz, 1H), 3.34-3.47 (m, 2H), 3.97 (d, J=8.8 Hz, 1H), 4.03 (d, J=6.0 Hz, 1H), 4.16 (d, J=9.6 Hz, 1H), 4.23-4.26 (m, 2H), 6.00-6.06 (br. m, 1H) ppm. MS (ESI) m/z: 339.95 (M+H)+, 337.94 (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-45b0125f6591488f933d6136984cf409
Source dataset
uspto-grants-2011_08
Patent number
US07994218B2

Reaction notes

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