{4-[(R)-2-Oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-butoxy}-acetic acid methyl ester → {4-[(R)-2-Oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-butoxy}-acetic Acid

HRID 489151Notes

Reaction equation

HRID 489151 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][O:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C@@H:15](/[CH:16]=[CH:17]/[C:18](=[O:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13][CH2:12][C:11]1=[O:27]>C(#N)C.P([O-])([O-])([O-])=O>[O:27]=[C:11]1[CH2:12][CH2:13][CH2:14][C@H:15](/[CH:16]=[CH:17]/[C:18](=[O:26])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:10]1[CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]([OH:28])=[O:2]

Participants

4

Reactant 1

HCID 11349716{4-[(R)-2-Oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-butoxy}-acetic acid methyl ester

Product 1

HCID 11303307{4-[(R)-2-Oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-butoxy}-acetic AcidYield 80%

Reagents, catalysts & solvents 2

HCID 1061PhosphateSolventHCID 6342AcetonitrileSolvent2×

Procedure

Rabbit liver esterase (134 units/mg, 1 mg) was added to a solution of {4-[(R)-2-oxo-6-((E)-3-oxo-4-phenyl-but-1-enyl)-piperidin-1-yl]-butoxy}-acetic acid methyl ester (10 mg, 0.026 mmol) in acetonitrile (0.2 mL) and pH 7.2 phosphate buffer (3.0 mL). After 24 h, acetonitrile (5 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 →3% MeOH(CH2Cl2, gradient) afforded 7.7 mg (80%) 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 →3% MeOH(CH2Cl2, gradient)

Sources & evidence

ORD record
ord-c159c918ab5c4836a7fc41622dfea5ea
Source dataset
uspto-grants-2005_12
Patent number
US06977260B2

Reaction notes

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