1-Benzhydrylamino-2-methylpropanephosphonous acid → 1-Amino-2-(3,4-dimethoxyphenyl)-ethanephosphonous acid

HRID 25994Notes

Reaction equation

HRID 25994 reaction equation
C([NH:14][CH:15]([P:27]([OH:29])[OH:28])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(NC(P(O)O)C(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[NH2:14][CH:15]([P:27]([OH:29])[OH:28])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH3:26])[CH:18]=1

Participants

3

Reactant 2

HCID 213258821-Benzhydrylamino-2-methylpropanephosphonous acidHCID 213258891-Benzhydrylamino-2-(3,4-dimethoxyphenyl)-ethanephosphonous acid

Product 1

HCID 213258641-Amino-2-(3,4-dimethoxyphenyl)-ethanephosphonous acid

Procedure

The procedure described in Example 36B was repeated using DL-1-benzhydrylamino-2-(3,4-dimethoxyphenyl)-ethanephosphonous acid (as obtained in Example 20) instead of DL-1-benzhydrylamino-2-methylpropanephosphonous acid to give DL-1-amino-2-(3,4-dimethoxyphenyl)-ethanephosphonous acid. This was treated with 60% hydrogen bromide at 80° followed by propylene oxide to give DL-1-amino-2-(3,4-dihydroxyphenyl)-ethanephosphonous acid, melting point 237°-238°, identical to that obtained in Example 20.

Sources & evidence

ORD record
ord-fbb7ac4887e442aea44109cf1f23a6c7
Source dataset
uspto-grants-1979_04
Patent number
US04147780

Reaction notes

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