Water → (R)-(4-chlorophenylcarbamoyloxy)phenylacetic acid

HRID 350673Notes

Reaction equation

HRID 350673 reaction equation
C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.[C:38]([OH:48])(=[O:47])[C@@H:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[OH:40].[Cl:49][C:50]1[CH:55]=[CH:54][C:53]([N:56]=[C:57]=[O:58])=[CH:52][CH:51]=1.O>ClCCl>[Cl:49][C:50]1[CH:55]=[CH:54][C:53]([NH:56][C:57]([O:40][C@H:39]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:38]([OH:48])=[O:47])=[O:58])=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 962WaterHCID 76934-Chlorophenyl IsocyanateHCID 11914(-)-Mandelic acidHCID 9809426Di-n-butyldilauryltin

Product 1

HCID 12992874(R)-(4-chlorophenylcarbamoyloxy)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.1 400 mg (0.63 mmol) of dibutyltin dilaurate are added to a solution of 10.0 g (65.7 mmol) of (R)-mandelic acid and 10.0 g (65.1 mmol) of 4-chlorophenyl isocyanate in 100 ml of dichloromethane, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is introduced into water and extracted with ethyl acetate. The organic phase is evaporated, giving (R)-(4-chlorophenylcarbamoyloxy)phenylacetic acid as a colourless solid; ESI 306.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is evaporated

Sources & evidence

ORD record
ord-7a132407b5124197aa44899b87a35e6f
Source dataset
uspto-grants-2007_02
Patent number
US07183277B2

Reaction notes

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