Tetrabutylammonium Fluoride → HCID 59954353, compound

HRID 1976251Notes

Reaction equation

HRID 1976251 reaction equation
[Si]([O:8][C@H:9]1[CH2:18][N:17]2[C@H:11]([CH2:12][N:13]([C:24](=[O:46])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:45])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:27][CH:26]=3)[C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]2=[O:19])[CH2:10]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[OH:8][C@H:9]1[CH2:18][N:17]2[C@H:11]([CH2:12][N:13]([C:24](=[O:46])[C:25]3[CH:30]=[CH:29][C:28]([NH:31][C:32](=[O:45])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[CH:27][CH:26]=3)[C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]2=[O:19])[CH2:10]1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70245362HCID 70245362, compound

Product 1

HCID 59954353HCID 59954353, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,11aS)-2-(tert-butyldimethylsilyloxy)-10-[4-[(2-phenylbenzoyl)amino]benzoyl]-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (5.53 g) prepared in Reference Example 68 in tetrahydrofuran (20 ml), there was dropwise added, with ice-cooling, a solution of tetrabutylammonium fluoride (4.54 g) in tetrahydrofuran (50 ml) over 5 minutes and the reaction solution was stirred at room temperature for 30 minutes. After the reaction solution was diluted with ethyl acetate, it was washed with water and then dried over anhydrous magnesium sulfate. The residue obtained after concentration of the reaction solution was subjected to silica gel column chromatography and then eluted with chloroform/acetone (1/1) to give 4.1 g (yield 91.0%) of the title compound.

Workup

  1. additionthere was dropwise added, with ice-
  2. temperaturecooling
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained after concentration of the reaction solution
  6. washeluted with chloroform/acetone (1/1)

Sources & evidence

ORD record
ord-b71b0e228b7240d29ec59468321f39f7
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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