Isobutyl iodide → HCID 178445448, compound

HRID 1464357Notes

Reaction equation

HRID 1464357 reaction equation
[OH:1][PH:2]([CH:4]([CH:21]([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])=[O:3].[CH2:42](I)[CH:43]([CH3:45])[CH3:44]>CS(C)=O>[OH:3][PH:2]([CH:4]([C:21]([CH2:42][CH:43]([CH3:45])[CH3:44])([C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:33])[C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]2[C:11]1=[O:20])=[O:1]

Participants

4

Reactant 2

HCID 10556Isobutyl iodideHCID 178525074HCID 178525074, compound

Product 1

HCID 178445448HCID 178445448, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.6 g of dibenzyl 2-(6-phthalimidohexylidene)malonate were added to a solution of 0.88 g of crystalline hypophosphorus acid in 10 ml of dry dichloromethane, the solution was cooled to 0° and then 2.8 g of triethylamine and 2.8 g of trimethylsilyl chloride were added. After stirring at room temperature for 3 hours, the mixture was poured into 60 ml of 1M hydrochloric acid and the resulting solution was extracted four times with dichloromethane. The combined extracts were dried and evaporated to give 3.9 g of a colorless gum containing crude dibenzyl 2-[1(RS)-(hydroxyphosphinyl)-6-phthalimidohexyl]malonate which was dissolved in 40 ml of dry dimethyl sulphoxide and reacted with isobutyl iodide in a manner analogous to that described in Example 10(ii). After purification of the crude product by chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution, there was obtained 2.0 g of dibenzyl 2-[1(RS)-(hydroxyphosphinyl)-6phthalimidohexyl]-2-isobutylmalonate as a colorless gum.

Workup

  1. customAfter purification of the crude product by chromatography on silica gel
  2. washfor the elution

Sources & evidence

ORD record
ord-137a1616fa3e48f0a658c2859f869b04
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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