Tributyltin Chloride → HCID 86591210, compound

HRID 1072351Notes

Reaction equation

HRID 1072351 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C@H:6]([C:22]([C:24]2[N:25]=[CH:26][N:27]3[CH:31]=[CH:30][S:29][C:28]=23)=[O:23])[CH2:5]1)=[N+:2]=[N-:3].[CH2:32]([Sn:36](Cl)([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])[CH2:33][CH2:34][CH3:35].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].C1COCC1>>[N:1]([C@@H:4]1[CH2:8][N:7]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C@H:6]([C:22]([C:24]2[N:25]=[CH:26][N:27]3[CH:31]=[C:30]([Sn:36]([CH2:37][CH2:38][CH2:39][CH3:40])([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:32][CH2:33][CH2:34][CH3:35])[S:29][C:28]=23)=[O:23])[CH2:5]1)=[N+:2]=[N-:3]

Participants

4

Reactant 3

HCID 15096Tributyltin ChlorideHCID 23714775LiHMDS tetrahydrofuranHCID 86591211HCID 86591211, compound

Product 1

HCID 86591210HCID 86591210, compound

Procedure

The title compound (321 mg) was prepared in substantially the same manner as in step c) of Synthesis Example 1, except that 585 mg of 7-[(2S,4S)-4-azido-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-2-yl]carbonylimidazo[5,1-b]thiazole, 0.396 ml of tri-n-butylstannyl chloride, and 2.8 ml of a 1.0 N lithium bis(trimethylsilyl)amide/THF solution were used as the starting materials.

Workup

  1. customof Synthesis Example 1

Sources & evidence

ORD record
ord-25ad5ccf70a54de780449b62d565a3e3
Source dataset
uspto-grants-2005_06
Patent number
US06908913B2

Reaction notes

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