Triisopropyl phosphite → HCID 53780404, compound

HRID 376178Notes

Reaction equation

[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:23]Br)=[CH:8][CH:9]([NH:20][CH:21]=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2].[P:25]([O:34]C(C)C)([O:30][CH:31]([CH3:33])[CH3:32])[O:26][CH:27]([CH3:29])[CH3:28]>>[C:1]([O:4][CH2:5][CH2:6][C:7]([CH2:23][P:25]([O:30][CH:31]([CH3:33])[CH3:32])([O:26][CH:27]([CH3:29])[CH3:28])=[O:34])=[CH:8][CH:9]([NH:20][CH:21]=[O:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 53954534HCID 53954534, compound

Product 1

HCID 53780404HCID 53780404, compound

Procedure

11.1 g (27.9 mmol) of benzyl 6-acetoxy-4-bromomethyl-2-formylamino-hex-3-enoate and 30.5 ml (111.5 mmol) of 90% triisopropyl phosphite are heated to 80° C. 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 over silica gel with ethyl acetate/isopropanol (7:1), giving benzyl 6-acetoxy-2-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate as an orange oil.

Workup

customExcess triisopropyl phosphite is removed by distillation
customthe residue is purified by chromatography over silica gel with ethyl acetate/isopropanol (7:1)

Sources & evidence

ORD record: ord-9cafca6c47e74f4cad7a1bba0a8669d8
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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