Tetrabutylammonium Fluoride → HCID 71523049, compound

HRID 1411260Notes

Reaction equation

HRID 1411260 reaction equation
[Si]([O:8][CH2:9][CH:10]([S:12][C:13]1[S:17][C:16]([NH:18][C:19]([N:21]2[C:37]3[C:32](=[CH:33][C:34]([Cl:38])=[CH:35][CH:36]=3)[C:23]3([CH2:27][CH2:26][N:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24]3)[CH2:22]2)=[O:20])=[N:15][CH:14]=1)[CH3:11])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[Cl:38][C:34]1[CH:33]=[C:32]2[C:23]3([CH2:27][CH2:26][N:25]([C:28]([O:30][CH3:31])=[O:29])[CH2:24]3)[CH2:22][N:21]([C:19](=[O:20])[NH:18][C:16]3[S:17][C:13]([S:12][CH:10]([CH3:11])[CH2:9][OH:8])=[CH:14][N:15]=3)[C:37]2=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 90449315HCID 90449315, compound

Product 1

HCID 71523049HCID 71523049, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 1-((5-((1-((t-butyldimethylsilyl)oxy)propan-2-yl)thio)thiazol-2-yl)carbamoyl)-5-chlorospiro[indoline-3,3′-pyrrolidine]-1′-carboxylate (200 mg, 0.34 mmol) was dissolved in tetrahydrofuran (10 mL). Thereafter, a tetrahydrofuran solution (0.2 mL, 1.7 mmol) of tetrabutylammonium fluoride (1 mol/mL) was added to the above obtained solution, and the thus obtained mixture was then stirred at room temperature for 11.3 hours. Thereafter, the reaction solution was concentrated in vacuo, and the obtained residue was then purified by preparative thin-layer chromatography (chloroform:methanol=10:1) to obtain the captioned compound (0.12 g, 72%) in the form of a white amorphous product.

Workup

  1. concentrationThereafter, the reaction solution was concentrated in vacuo
  2. customthe obtained residue was then purified by preparative thin-layer chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-d59ae075ff3f4e94b93ca2aaca7bcb36
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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