Water → HCID 67785431, compound

HRID 1612781Notes

Reaction equation

HRID 1612781 reaction equation
C(OC([NH:8][CH2:9][C:10]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([OH:24])[CH2:11][P:12]([CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:16])[O:13]CC)=O)(C)(C)C.C[Si](C)(C)[Br:34].O>ClCCl.CO>[BrH:34].[NH2:8][CH2:9][C:10]([C:25]1[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=1)([OH:24])[CH2:11][P:12]([CH:17]([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:13])[OH:16]

Participants

6

Reactant 3

HCID 962WaterHCID 76113BromotrimethylsilaneHCID 57288295HCID 57288295, compound

Product 1

HCID 67785431HCID 67785431, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.48 g of ethyl 3-(N-tert.-butoxycarbonylamino)-2-(4-chlorophenyl)-2-hydroxy-propyl(diethoxymethyl)phosphinate in 10 ml of anhydrous dichloromethane is treated with 0.76 g of trimethylbromosilane and the resulting colourless solution stirred for 24 hours at room temperature under an inert atmosphere. The volatile materials are removed under reduced pressure to give a foam which is redisslued in 5 ml of methanol containing 1% of water and the solution stirred for 20 hours at room temperature. After this time evaporation of the solvent in vacuo followed by chromatography of the residue on reverse-phase silicagel and drying of the off white solid thus obtained in high vacuum gives 3-amino-2-(4-chlorophenyl)-2-hydroxypropyl(diethoxymethyl)phosphinic acid hydrobromide salt. Dissolution of the salt in the methanol and treatment with propylene oxide gives 3-amino-2-(4-chlorophenyl)-2-hydroxy-propyl(diethoxymethyl)phosphinic acid; 1H-NMR (D2O): δ(ppm)=7.39 (4H, m, Ph), 4.75 (1H, d, CH--P), 3.67-3.23 (6H, m, 2×CH2CO+CH 2 N), 2.38-1.97 (2H, ABq, CH2P), 1.23-1.04 (6H, t, 2×CH3).

Workup

  1. customThe volatile materials are removed under reduced pressure
  2. customto give a foam which
  3. stirringthe solution stirred for 20 hours at room temperature
  4. customAfter this time evaporation of the solvent in vacuo
  5. customdrying of the off white solid
  6. customthus obtained in high vacuum

Sources & evidence

ORD record
ord-fb7e823e3ada4bc598a81715f430f956
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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