Lithium Hexamethyldisilazide → HCID 89962088, compound

HRID 337913

Reaction equation

HRID 337913 reaction equation
[S:1]1[CH:5]=[C:4]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[N:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:24][C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[C:27]([F:32])[C:26]=1[S:33](Cl)(=[O:35])=[O:34]>C1COCC1>[S:1]1[CH:5]=[C:4]([N:6]([S:33]([C:26]2[C:27]([F:32])=[CH:28][C:29]([F:31])=[CH:30][C:25]=2[F:24])(=[O:35])=[O:34])[C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 2733832Lithium HexamethyldisilazideHCID 27769832,4,6-Trifluorobenzenesulfonyl chlorideHCID 53241636tert-butyl N-(1,3-thiazol-4-yl)carbamate

Product 1

HCID 89962088HCID 89962088, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction and aftertreatment were conducted in the same manner as in Example 86a by using tert-butyl 1,3-thiazol-4-ylcarbamate (Synthesis, 2010, 3152-3162; 1.00 g, 4.99 mmol), lithium bis(trimethylsilyl)amide (1.0 M solution in THF; 5.99 mL, 5.99 mmol), 2,4,6-trifluorobenzenesulfonyl chloride (1.38 g, 5.99 mmol) and THF (15 mL), to yield the title compound (1.53 g, 78%) as a pale yellow solid.

Workup

  1. customThe reaction and aftertreatment

Sources & evidence

ORD record
ord-54d4b39789334dc0b2febdb3aa5de7f5
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Linked notes

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