Triethyl phosphite → 8-(N-benzyloxycarbonylamino)-4-diethylphosphonomethyl-2-formylamino-oct-3-enoic acid methyl ester

HRID 376111Notes

Reaction equation

HRID 376111 reaction equation
[P:1]([O:8]CC)([O:5][CH2:6][CH3:7])[O:2][CH2:3][CH3:4].[CH3:11][O:12][C:13](=[O:37])[CH:14]([NH:34][CH:35]=[O:36])[CH:15]=[C:16]([CH2:32]Br)[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>>[CH3:11][O:12][C:13](=[O:37])[CH:14]([NH:34][CH:35]=[O:36])[CH:15]=[C:16]([CH2:32][P:1]([O:2][CH2:3][CH3:4])([O:5][CH2:6][CH3:7])=[O:8])[CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 544393678-(N-benzyloxycarbonylamino)-4-bromomethyl-2-formylamino-oct-3-enoic acid methyl ester

Product 1

HCID 542340138-(N-benzyloxycarbonylamino)-4-diethylphosphonomethyl-2-formylamino-oct-3-enoic acid methyl ester

Procedure

5 ml of triethyl phosphite are added to 1.45 g (3.3 mmol) of 8-(N-benzyloxycarbonylamino)-4-bromomethyl-2-formylamino-oct-3-enoic acid methyl ester, and the mixture is heated at 75° for 8 hours with stirring. The excess triethyl phosphite is distilled off under reduced pressure to give an oily residue which is purified by chromatography on a silica gel column with first ethyl acetate and then ethyl acetate/methanol (9:1). 8-(N-benzyloxycarbonylamino)-4-diethylphosphonomethyl-2-formylamino-oct-3-enoic acid methyl ester is obtained.

Workup

  1. temperaturethe mixture is heated at 75° for 8 hours
  2. distillationThe excess triethyl phosphite is distilled off under reduced pressure
  3. customto give an oily residue which
  4. customis purified by chromatography on a silica gel column with first ethyl acetate

Sources & evidence

ORD record
ord-6a4c3b47e5524b7c9b7bbe686132e6c9
Source dataset
uspto-grants-1996_01
Patent number
US05488140

Reaction notes

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