Benzyl chloroformate → HCID 178523200, compound

HRID 1058758Notes

Reaction equation

HRID 1058758 reaction equation
[NH2:1][CH:2]([PH:10](=[O:12])[OH:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>O1CCOCC1.O>[C:4]1([CH2:3][CH:2]([PH:10](=[O:11])[OH:12])[NH:1][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2×HCID 178510800HCID 178510800, compound

Product 1

HCID 178523200HCID 178523200, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
20 °C

Procedure

To a solution of 7 g (37.8 mmol) of (1-amino-2-phenylethyl)phosphinic acid in 86 ml of a mixture of dioxane and water, in the presence of one equivalent of sodium hydroxide (1.51 g), are added dropwise, at 0° C and simultaneously, a solution of 7.55 g (44.26 mmol) of benzyl chloroformate in 21 ml of dioxane and, in order to keep the pH of the reaction at about 9, a solution of 2.42 g of sodium hydroxide in 21 ml of water. At the end of the addition, the mixture is maintained at a temperature in the region of 20° C. for 2 hours. The aqueous phase is then washed with 3 times 20 ml of diethyl ether. The aqueous phase is acidified, at 0° C., with vigorous stirring, using 27 ml of 6N hydrochloric acid solution. The abundant white precipitate formed is filtered off, washed with water and dried. 12.08 g of product are recovered (yield=83.7%).

Workup

  1. customthe pH of the reaction at about 9
  2. additionAt the end of the addition
  3. washThe aqueous phase is then washed with 3 times 20 ml of diethyl ether
  4. customis acidified, at 0° C., with vigorous stirring
  5. customThe abundant white precipitate formed
  6. filtrationis filtered off
  7. washwashed with water
  8. customdried
  9. custom12.08 g of product are recovered (yield=83.7%)

Sources & evidence

ORD record
ord-93f1f0286f0e4ceca30f4354345ad087
Source dataset
uspto-grants-2003_02
Patent number
US06518260B1

Reaction notes

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