Tetrabutylammonium Fluoride → HCID 58822274, compound

HRID 546480Notes

Reaction equation

HRID 546480 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([CH2:15][O:16][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11][C@@H:10]1[NH:34][C:35]([C:37]1[S:38][C:39]2[CH2:40][N:41]([CH3:46])[CH2:42][CH2:43][C:44]=2[N:45]=1)=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@@H:12]([CH2:15][OH:16])[CH2:11][C@@H:10]1[NH:34][C:35]([C:37]1[S:38][C:39]2[CH2:40][N:41]([CH3:46])[CH2:42][CH2:43][C:44]=2[N:45]=1)=[O:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57864676HCID 57864676, compound

Product 1

HCID 58822274HCID 58822274, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S,2S,4R)—N1-tert-Butoxycarbonyl-4-(tert-butyldiphenylsilyloxymethyl)-N2-[(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)carbonyl]-1,2-cyclohexanediamine (1.25 g) was dissolved in tetrahydrofuran (30 ml), and tetrabutylammonium fluoride (1 M solution, 2.5 ml), and the mixture was stirred at room temperature for 3 days. After the solvent was distilled off under reduced pressure, dichloromethane was added, and the reaction mixture was washed with water, the resultant organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:20→1:10) to obtain the title compound (540 mg) as a pale yellow amorphous substance.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, dichloromethane
  2. additionwas added
  3. washthe reaction mixture was washed with water
  4. dry with materialthe resultant organic layer was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (methanol:dichloromethane=1:20→1:10)

Sources & evidence

ORD record
ord-a2eadf6e38e44e088a0973f426be5d68
Source dataset
uspto-grants-2011_05
Patent number
US07935824B2

Reaction notes

Loading…