Tributyltin Chloride → HCID 23449050, compound

HRID 989859Notes

Reaction equation

HRID 989859 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:60]=[CH:59][C:36]([CH2:37][O:38][C:39]([NH:41][CH2:42][CH2:43][S:44]([NH:47][CH2:48][C:49]([C:51]2[N:52]=[CH:53][N:54]3[CH:58]=[CH:57][S:56][C:55]=23)=[O:50])(=[O:46])=[O:45])=[O:40])=[CH:35][CH:34]=1)([O-:32])=[O:31].[Cl-].[NH4+]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[N+:30]([C:33]1[CH:34]=[CH:35][C:36]([CH2:37][O:38][C:39]([NH:41][CH2:42][CH2:43][S:44]([NH:47][CH2:48][C:49]([C:51]2[N:52]=[CH:53][N:54]3[CH:58]=[C:57]([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:56][C:55]=23)=[O:50])(=[O:46])=[O:45])=[O:40])=[CH:59][CH:60]=1)([O-:32])=[O:31]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 25517Ammonium ChlorideHCID 23449338HCID 23449338, compoundHCID 23714775LiHMDS tetrahydrofuran

Product 1

HCID 23449050HCID 23449050, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

Tri-n-butylstannyl chloride (0.83 ml) and 7.3 ml of a 1.0 N lithiumbis(trimethylsilyl)amide/THF solution were sequentially added at −73° C. in an argon atmosphere to a solution of 682 mg of 7-[2-(4-Nitrobenzyloxycarbonyl)aminoethane-sulfonylamino]acetylimidazo[5,1-b]thiazole in 16 ml of THF and 3 ml of HMPA. The mixture was stirred at the same temperature for 30 min. An aqueous ammonium chloride solution was added to the reaction solution. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1-1:2) to give 327 mg of the title compound.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1-1:2)

Sources & evidence

ORD record
ord-3ebbe17d104a4d648f2ec13322782253
Source dataset
uspto-grants-2002_10
Patent number
US06458780B1

Reaction notes

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