Phosphate → HCID 9977908, compound

HRID 1582214Notes

Reaction equation

HRID 1582214 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:14](=[O:15])[CH2:13][CH2:12][C@@H:11]1/[CH:16]=[CH:17]/[C:18](=[O:27])[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1.P([O-])([O-])([O-])=O>C(#N)C>[Cl:26][C:22]1[CH:21]=[C:20]([CH2:19][C:18](=[O:27])/[CH:17]=[CH:16]/[C@H:11]2[CH2:12][CH2:13][C:14](=[O:15])[N:10]2[CH2:9][CH2:8][CH2:7][CH2:6][O:5][CH2:4][C:3]([OH:28])=[O:2])[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 1061PhosphateHCID 10069989HCID 10069989, compound

Product 1

HCID 9977908HCID 9977908, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (2.4 mg, 0.006 mmol), rabbit liver esterase (1 mg, 134 units/mg), pH 7.2 phosphate buffer (2.5 mL) and acetonitrile (0.1 mL) was stirred together at rt for 18 h. Acetonitrile (5 mL) was then added and the mixture was concentrated in vacuo to dryness. The residue was purified by flash column chromatography (0%→10% MeOH/CH2Cl2) to afford 1.1 mg (47%) of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid.

Workup

  1. concentrationthe mixture was concentrated in vacuo to dryness
  2. customThe residue was purified by flash column chromatography (0%→10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f7e42aa3299449d3aa637c41e9b3bb31
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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