Phosphate → HCID 14549129, compound

HRID 1729139Notes

Reaction equation

HRID 1729139 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 39.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

29.9 g (0.08 mol) of IV-15 was mixed with 800 ml of 0.1M phosphate buffer (pH 7.5), 30 ml of chloroform and 6 g of Amano Lipase P and the mixture was stirred vigorously at 30°-35° C. for 20 hours. The reaction mixture was extracted with 600 ml of methyl isobutyl ketone. The organic layer was concentrated under reduced pressure and the residue was purified by column chromatography using a 12:1 mixed solution of chloroform and ethyl acetate as eluting solvent to obtain 10.6 g of (+)-benzyl 4'-(1-hydroxyethyl)-4-biphenylcarboxylate (V-15). [α]D25 =+23.7° (c=1, CHCl3), m.p.=104°-106° C.

Workup

  1. extractionThe reaction mixture was extracted with 600 ml of methyl isobutyl ketone
  2. concentrationThe organic layer was concentrated under reduced pressure
  3. customthe residue was purified by column chromatography
  4. washas eluting solvent

Sources & evidence

ORD record
ord-89c349c280724e6881bc36f189d09632
Source dataset
uspto-grants-1994_07
Patent number
US05332675

Reaction notes

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