Phosphate → HCID 14549129, compound

HRID 1729144Notes

Reaction equation

HRID 1729144 reaction equation
C([O:4][CH:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)[CH3:6])(=O)C.P([O-])([O-])([O-])=O>C(Cl)(Cl)Cl>[OH:4][CH:5]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:15][CH:14]=2)=[CH:11][CH:12]=1)[CH3:6]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 14534380HCID 14534380, compound

Product 1

HCID 14549129HCID 14549129, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

15 g of benzyl (-)-4'-(1-acetoxyethyl)-4-biphenylcarboxylate, 10 ml of chloroform, 400 ml of 0.2M phosphate buffer and 3 g of Amano swine liver esterase were mixed and reacted at 30°-35° C. for 30 hours. The reaction solution was extracted with chloroform. The chloroform layer was concentrated and the residue was column-chromatographed to give 11.8 g of (-)-benzyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (V-26).

Workup

  1. customreacted at 30°-35° C. for 30 hours
  2. extractionThe reaction solution was extracted with chloroform
  3. concentrationThe chloroform layer was concentrated
  4. customthe residue was column-chromatographed

Sources & evidence

ORD record
ord-b8cc0f1c11b44544b95e9bf901eb6c8d
Source dataset
uspto-grants-1994_07
Patent number
US05332675

Reaction notes

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