Tributyltin Chloride → HCID 22631454, compound

HRID 1840429Notes

Reaction equation

HRID 1840429 reaction equation
[CH2:1]([Sn:5](Cl)([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1.[N+:30]([C:33]1[CH:55]=[CH:54][C:36]([CH2:37][O:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][S:45][C:46]2[N:47]=[CH:48][N:49]3[CH:53]=[CH:52][S:51][C:50]=23)=[O:40])=[CH:35][CH:34]=1)([O-:32])=[O:31].[Cl-].[NH4+]>C1COCC1>[N+:30]([C:33]1[CH:34]=[CH:35][C:36]([CH2:37][O:38][C:39]([NH:41][CH2:42][CH2:43][CH2:44][S:45][C:46]2[N:47]=[CH:48][N:49]3[CH:53]=[C:52]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:1][CH2:2][CH2:3][CH3:4])[S:51][C:50]=23)=[O:40])=[CH:54][CH:55]=1)([O-:32])=[O:31]

Participants

6

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 22631774HCID 22631774, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 22631454HCID 22631454, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tri-n-butylstannyl chloride (1.21 ml) and 9.47 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were added to a solution of 1.11 g of 7-[3-(4-nitrobenzyloxycarbonyl)aminopropyl]thioimidazo[5,1-b]thiazole in 28 ml of THF at −45° C. under an argon atmosphere, and the mixture was stirred for one hr. An aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate, followed by washing with brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to prepare 1.24 g of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washby washing with brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then removed by distillation
  5. customthe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)
  6. customto prepare 1.24 g of the title compound

Sources & evidence

ORD record
ord-f2185ee6752942a8acf3812262fddafc
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

Loading…