Water → HCID 131717706, compound

HRID 1682252Notes

Reaction equation

HRID 1682252 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[N+:12]([C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1)([O-:14])=[O:13].C(N(CC)CC)C.O>CN(C=O)C>[C:1]([O:11][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 11914(-)-Mandelic acidHCID 660114-Nitrobenzyl bromide

Product 1

HCID 131717706HCID 131717706, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 15.2 g (100 mmol) of D-mandelic acid, 21.6 g (100 mmol) of 4-nitrobenzyl bromide, and 14.0 ml (100 mmol) of triethylamine in 300 ml of DMF was stirred for 8 hours at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N hydrochloric acid and water and recrystallized from ether-petroleum ether to give 19.6 g of the aimed product D-4 in 68% yield.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 2N hydrochloric acid and water
  3. customrecrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-ebb93b0b150a45a8bd7874c8eee86a6b
Source dataset
uspto-grants-1992_12
Patent number
US05175341

Reaction notes

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