t-butyl N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)propionyl]-3-aminopropionate → N-(2-(phosphonomethylamino)-3-(4-biphenylyl)propionyl)-3-aminopropionic acid

HRID 487221Notes

Reaction equation

HRID 487221 reaction equation
C[O:2][P:3]([CH2:7][NH:8][CH:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:25][CH:24]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])=[O:11])([O:5]C)=[O:4]>Br>[P:3]([CH2:7][NH:8][CH:9]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:27][CH:28]=1)[C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])([OH:5])([OH:4])=[O:2]

Participants

3

Reactant 1

HCID 19094421t-butyl N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)propionyl]-3-aminopropionate

Product 1

HCID 9866029N-(2-(phosphonomethylamino)-3-(4-biphenylyl)propionyl)-3-aminopropionic acid

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of t-butyl N-[2-(dimethylphosphonomethylamino)-3-(4-biphenylyl)propionyl]-3-aminopropionate (0.38 g, 0.78 mmol) in 30% HBr/glacial HOAc is stirred at room temperature for 6.5 hours. After concentration to about 1/10 volume, ether (40 mL) is added and the solid filtered. The solid is then suspended in water (3 mL), filtered off and washed with water to obtain N-[2-(phosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionic acid, m.p. 242°-244° dec.

Workup

  1. concentrationAfter concentration to about 1/10 volume, ether (40 mL)
  2. additionis added
  3. filtrationthe solid filtered
  4. filtrationfiltered off
  5. washwashed with water

Sources & evidence

ORD record
ord-50c525c6fa2148069de101efb3dda14e
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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