Triisopropyl phosphite → HCID 53768570, compound

HRID 376170Notes

Reaction equation

[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7]([CH2:18]Br)=[CH:8][CH:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2].[P:21]([O:30]C(C)C)([O:26][CH:27]([CH3:29])[CH3:28])[O:22][CH:23]([CH3:25])[CH3:24]>>[C:1]([O:4][CH:5]([CH3:20])[CH2:6][C:7]([CH2:18][P:21]([O:26][CH:27]([CH3:29])[CH3:28])([O:22][CH:23]([CH3:25])[CH3:24])=[O:30])=[CH:8][CH:9]([NH:15][CH:16]=[O:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 54248109HCID 54248109, compound

Product 1

HCID 53768570HCID 53768570, compound

Procedure

18.0 g (51.4 mmol) of ethyl 6-acetoxy-4-bromomethyl-2-formylamino-hept-3-enoate and 56.3 ml (205.6 mmol) of 90% triisopropyl phosphite are heated to 80° C. and and the mixture is stirred for 18 hours under a pressure of 100-150 mbar. Excess triisopropyl phosphite is removed by distillation and the residue is purified by chromatography on silica gel with ethyl acetate/isopropanol (7:2), giving ethyl 6-acetoxy-2-formylamino-4-diisopropylphosphonomethyl-hept-3-enoate as an orange oil. yield.

Workup

customExcess triisopropyl phosphite is removed by distillation
customthe residue is purified by chromatography on silica gel with ethyl acetate/isopropanol (7:2)

Sources & evidence

ORD record: ord-b2a2283682234e308e10b5b0266f45e3
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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