Triisopropyl phosphite → HCID 86747670, compound

HRID 376161Notes

Reaction equation

Br[CH2:2][C:3]([CH2:14][CH2:15][O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][CH:5]([NH:11][CH:12]=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[P:23]([O:32]C(C)C)([O:28][CH:29]([CH3:31])[CH3:30])[O:24][CH:25]([CH3:27])[CH3:26]>>[CH2:21]([O:20][C:18]([CH2:17][O:16][CH2:15][CH2:14][C:3]([CH2:2][P:23]([O:28][CH:29]([CH3:31])[CH3:30])([O:24][CH:25]([CH3:27])[CH3:26])=[O:32])=[CH:4][CH:5]([NH:11][CH:12]=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:19])[CH3:22]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 54432351HCID 54432351, compound

Product 1

HCID 86747670HCID 86747670, compound

Procedure

9 g (23.7 mmol) of ethyl 4-bromomethyl-6-ethoxycarbonylmethoxy-2-formylaminohex-3-enoate and 23.3 ml (94.8 mmol) of triisopropyl phosphite (90%) are heated to 80° C. and stirred for 18 hours under a pressure of 100 mbar. Excess triisopropyl phosphite is removed by distillation and the residue is chromatographed on silica gel with hexane/ethyl acetate 1:3 and then with hexane/ethyl acetate/ethanol (1:3:5%) giving ethyl 6-ethoxycarbonylmethoxy-2-formylamino-4-diisopropylphosphonomethyl-hex-3-enoate as a yellow oil.

Workup

customExcess triisopropyl phosphite is removed by distillation
customthe residue is chromatographed on silica gel with hexane/ethyl acetate 1:3

Sources & evidence

ORD record: ord-a101b42b926d4145a4ad889c4f90ac5e
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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