Hydrochloric Acid → HCID 9977908, compound

HRID 1582216Notes

Reaction equation

HRID 1582216 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[CH2:16][CH2:17][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.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 66884727HCID 66884727, compound

Product 1

HCID 9977908HCID 9977908, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (4-{(R)-2-[4-(3-chlorophenyl)-3-oxo-butyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid methyl ester (8.1 mg, 0.02 mmol), rabbit liver esterase (1 mg, 134 units/mg), pH 7.2 phosphate buffer (3 mL) and acetonitrile (0.1 mL) was stirred together at rt for 16.5 h. Aqueous HCl (0.5 M, 5 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic phase was dried (Na2SO4), filtered and concentrated in vacuo to afford 1.6 mg (20%) of (4-{(R)-2-[(E)-4-(3-chlorophenyl)-3-oxo-but-1-enyl]-5-oxo-pyrrolidin-1-yl}-butoxy)-acetic acid.

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (3×5 mL)
  2. dry with materialThe combined organic phase was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01389ce1019b4c9ab8c879750a5ec027
Source dataset
uspto-grants-2004_05
Patent number
US06734206B1

Reaction notes

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