Tetrabutylammonium Fluoride → HCID 59586749, compound

HRID 218541Notes

Reaction equation

HRID 218541 reaction equation
[Si]([O:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]2[CH:32]=[CH:31][C:30]([N:33]3[CH2:37][C@H:36]([CH2:38][NH:39][C:40]([C:42]4[S:43][C:44]([Cl:47])=[CH:45][CH:46]=4)=[O:41])[O:35][C:34]3=[O:48])=[CH:29][C:28]=2[C:49]([F:52])([F:51])[F:50])[C:22]1=[O:53])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:47][C:44]1[S:43][C:42]([C:40]([NH:39][CH2:38][C@@H:36]2[O:35][C:34](=[O:48])[N:33]([C:30]3[CH:31]=[CH:32][C:27]([N:23]4[CH2:24][CH2:25][CH2:26][N:21]([CH2:20][CH2:19][OH:18])[C:22]4=[O:53])=[C:28]([C:49]([F:51])([F:50])[F:52])[CH:29]=3)[CH2:37]2)=[O:41])=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59586673HCID 59586673, compound

Product 1

HCID 59586749HCID 59586749, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 8.88 g (11.3 mmol) of the product from example 73A in 225 ml of THF is admixed with 6.95 g (26.6 mmol) of a 1 molar solution of tetrabutylammonium fluoride in THF. The mixture is stirred at RT for 45 min. Then it is freed of the solvent and the residue is purified by chromatography on silica gel (40:1→10:1 dichloromethane/methanol). This affords 5.24 g (80% of theory) of the desired product.

Workup

  1. customthe residue is purified by chromatography on silica gel (40:1→10:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-143b378ef79c4a21a2b30379caaea390
Source dataset
uspto-grants-2012_06
Patent number
US08198267B2

Reaction notes

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