Tetrabutylammonium Fluoride → HCID 86748816, compound

HRID 1648461Notes

Reaction equation

HRID 1648461 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([O:32][Si](C(C)(C)C)(C)C)[CH2:9][NH:10][C@H:11]([CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:32])[CH2:9][NH:10][C@H:11]([CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:12][O:13][C:14]2[CH:27]=[CH:26][C:17]([CH2:18][CH:19]3[S:23][C:22](=[O:24])[NH:21][C:20]3=[O:25])=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 88459543HCID 88459543, compound

Product 1

HCID 86748816HCID 86748816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A procedure similar to that described in Preparation 4, above, was followed, but using 350 mg of 5-(4-{2(R)-[2(R)-(3-chlorophenyl)-2-t-butyldimethylsilyloxyethylamino]-4-methylpentyloxy}benzyl]thiazolidine-2,4 -dione [prepared as described in Preparation 18], 1,39 g of tetrabutyl ammonium fluoride and 10 ml of tetrahydrofuran to obtain the title compound in crude form. This crude product was then purified by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, to give 180 mg of the title compound, having an Rf=0.28 (thin layer chromatography on silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Workup

  1. customA procedure similar to that described in Preparation 4

Sources & evidence

ORD record
ord-81a0ef4767c74431b8731affb31da0b5
Source dataset
uspto-grants-1995_07
Patent number
US05436257

Reaction notes

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