Triisopropyl phosphite → HCID 54415170, compound

HRID 376154Notes

Reaction equation

Br[CH2:2][C:3]([CH2:14][CH2:15][CH2:16][O:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][CH:5]([NH:11][CH:12]=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7].[P:24]([O:33]C(C)C)([O:29][CH:30]([CH3:32])[CH3:31])[O:25][CH:26]([CH3:28])[CH3:27]>>[CH2:22]([O:21][C:19]([CH2:18][O:17][CH2:16][CH2:15][CH2:14][C:3]([CH2:2][P:24]([O:29][CH:30]([CH3:32])[CH3:31])([O:25][CH:26]([CH3:28])[CH3:27])=[O:33])=[CH:4][CH:5]([NH:11][CH:12]=[O:13])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:20])[CH3:23]

Participants

Reactant 2

HCID 8304Triisopropyl phosphite

HCID 53648515HCID 53648515, compound

Product 1

HCID 54415170HCID 54415170, compound

Procedure

6.4 g (15 mmol) of ethyl 4-bromomethyl-7-ethoxycarbonylmethoxy-2-formylamino-hept-3-enoate and 14.8 ml (60 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 over silica gel with hexane/ethyl acetate (1:2:5%) to give ethyl 7-ethoxycarbonylmethoxy-2-formylamino-4-diisopropylphosphonomethyl-hept-3-enoate as a brown oil.

Workup

customExcess triisopropyl phosphite is removed by distillation
customthe residue is chromatographed over silica gel with hexane/ethyl acetate (1:2:5%)

Sources & evidence

ORD record: ord-5c0a217fdaf648e6a97b000321f3f70b
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488140

Reaction notes

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