Triisopropyl phosphite → diethyl E-2-formylamino-4-diisopropylphosphonomethyl-hept-3-ene-1,7-dicarboxylate

HRID 654657Notes

Reaction equation

HRID 654657 reaction equation
[CH:1]([NH:3][CH:4]([CH:11]=[C:12]([CH2:21]Br)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[CH:23]([O:26][P:27]([O:32]C(C)C)[O:28][CH:29]([CH3:31])[CH3:30])([CH3:25])[CH3:24]>>[CH:1]([NH:3][CH:4](/[CH:11]=[C:12](/[CH2:21][P:27]([O:28][CH:29]([CH3:31])[CH3:30])([O:26][CH:23]([CH3:25])[CH3:24])=[O:32])\[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2]

Participants

3

Reactant 2

HCID 8304Triisopropyl phosphiteHCID 54128616Diethyl 2-formylamino-4-bromomethyl-hept-3-ene-1,7-dicarboxylate

Product 1

HCID 86746005diethyl E-2-formylamino-4-diisopropylphosphonomethyl-hept-3-ene-1,7-dicarboxylate

Procedure

8.7 g (25 mmol) of diethyl 2-formylamino-4-bromomethyl-hept-3-ene-1,7-dicarboxylate and 21 ml (75 mmol) of triisopropylphosphite (90%) are heated to 80°-90° C. and the mixture is stirred for 19 hours under a pressure of ca. 100 mbar. Excess triisopropylphosphite is removed by distillation and the residue obtained after evaporation is chromatographed over 150 g of silica gel first with ethyl acetate and then with ethyl acetate/ethanol (9:1) as eluant, giving diethyl E-2-formylamino-4-diisopropylphosphonomethyl-hept-3-ene-1,7-dicarboxylate as a yellowish oil.

Workup

  1. customExcess triisopropylphosphite is removed by distillation
  2. customthe residue obtained
  3. customafter evaporation
  4. customis chromatographed over 150 g of silica gel first with ethyl acetate

Sources & evidence

ORD record
ord-304b0213385a4fb189107f86f3cfb708
Source dataset
uspto-grants-1992_07
Patent number
US05134134

Reaction notes

Loading…