HCID 11632828, compound → HCID 11581922, compound

HRID 2114751Notes

Reaction equation

HRID 2114751 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][S:7][CH2:8][CH2:9][N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][C@@H:11]1/[CH:17]=[CH:18]/[CH:19]([OH:27])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(#N)C.P([O-])([O-])([O-])=O>[OH:27][CH:19]([CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)/[CH:18]=[CH:17]/[C@H:11]1[CH2:12][CH2:13][CH2:14][C:15](=[O:16])[N:10]1[CH2:9][CH2:8][S:7][CH2:6][CH2:5][CH2:4][C:3]([OH:28])=[O:2]

Participants

4

Reactant 1

HCID 11632828HCID 11632828, compound

Product 1

HCID 11581922HCID 11581922, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6342AcetonitrileSolvent2×

Procedure

Rabbit liver esterase (134 units/mg, 1 mg) was added to a solution of 4-{2-[(R)-2-((E)-3-hydroxy-4-phenyl-but-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric acid methyl ester (5.2 mg, 0.013 mmol) in acetonitrile (0.2 mL) and pH 7.2 phosphate buffer (3.0 mL). After 24 h, acetonitrile (10 mL) was added and the reaction mixture was concentrated to dryness in vacuo. Purification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient) afforded 4.7 mg (94%) of the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo
  2. customPurification of the residue by flash column chromatography on silica gel (CH2Cl2→5% MeOH/CH2Cl2, gradient)

Sources & evidence

ORD record
ord-1880606e7639433f84d6c65316cabe8c
Source dataset
uspto-grants-2008_10
Patent number
US07435746B2

Reaction notes

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