Triethyl phosphite → HCID 86743851, compound

HRID 2073269Notes

Reaction equation

HRID 2073269 reaction equation
Br[CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[C@@H:7]1[CH2:11][C@@H:10]([NH:12][S:13]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:9][N:8]1[S:23]([C:26]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[P:33]([O:40]CC)([O:37][CH2:38][CH3:39])[O:34][CH2:35][CH3:36]>>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([S:23]([N:8]2[CH2:9][C@H:10]([NH:12][S:13]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH2:11][C@H:7]2/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][P:33]([O:37][CH2:38][CH3:39])([O:34][CH2:35][CH3:36])=[O:40])(=[O:25])=[O:24])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 67864106HCID 67864106, compound

Product 1

HCID 86743851HCID 86743851, compound

Procedure

A mixture of (2S,4R)-2-[(Z)-5-bromo-1-pentenyl]-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)pyrrolidine (200 mg) and triethyl phosphite (5.0 ml) was refluxed for 3 hours and evaporated in vacuo to give an oil. The oil was chromatographed on silica gel column with chloroform as an eluent to give (2S,4R)-1-(4-chlorophenylsulfonyl)-4-(4-chlorophenylsulfonylamino)-2-[(Z)-5-diethoxyphosphoryl-1-pentenyl]pyrrolidine (164 mg) as an oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customevaporated in vacuo
  3. customto give an oil
  4. customThe oil was chromatographed on silica gel column with chloroform as an eluent

Sources & evidence

ORD record
ord-115b108015ba43e78d8181ccafbf9462
Source dataset
uspto-grants-1990_04
Patent number
US04916152

Reaction notes

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