Benzyl chloroformate → HCID 178523200, compound

HRID 231937Notes

Reaction equation

HRID 231937 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]>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

5

Reactant 3

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

Product 1

HCID 178523200HCID 178523200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(1-Amino-2-phenylethyl)phosphinic acid (1 g., 5.4 mmole) is suspended in water (25 ml.) at 0° and the pH is adjusted to 9.5 with concentrated sodium hydroxide solution. Benzyl chloroformate (0.9 ml., 1.08 g., 6.3 mmole) is added while the pH is maintained at 9.5 by the addition of sodium hydroxide. After the pH stabilizes, the mixture is stirred for 3 hours at room temperature. The basic solution is washed with ether and then acidified. The white solid precipitate is collected on a frit to give [2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]-phosphinic acid. TLC (silica gel; isopropanol:ammonia:water, 7:2:1) Rf =0.75.

Workup

  1. washThe basic solution is washed with ether
  2. customThe white solid precipitate is collected on a frit

Sources & evidence

ORD record
ord-9870082414104e3facb55a5def69aca8
Source dataset
uspto-grants-1989_07
Patent number
US04849414

Reaction notes

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