HCID 67785431, compound → HCID 19776495, compound

HRID 1612782Notes

Reaction equation

HRID 1612782 reaction equation
Br.[NH2:2][CH2:3][C:4]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([OH:16])[CH2:5][P:6]([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=[O:8])[OH:7]>C1OC1C>[NH2:2][CH2:3][C:4]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)([OH:16])[CH2:5][P:6]([CH:9]([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])(=[O:7])[OH:8]

Participants

3

Reactant 1

HCID 67785431HCID 67785431, compound

Product 1

HCID 19776495HCID 19776495, compound

Reagents, catalysts & solvents 1

HCID 6378Propylene OxideSolvent

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).

Sources & evidence

ORD record
ord-d9721a5b587943a88a1812a5f9297c0a
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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