Tetrabutylammonium Fluoride → HCID 12044205, compound

HRID 990077Notes

Reaction equation

HRID 990077 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][S:15]([C:18]3[CH:49]=[CH:48][C:21]([CH2:22][CH2:23][NH:24][CH2:25][C@H:26]([OH:47])[CH2:27][O:28][C:29]4[CH:34]=[CH:33][C:32]([O:35][Si](C(C)C)(C(C)C)C(C)C)=[C:31]([CH3:46])[CH:30]=4)=[CH:20][CH:19]=3)(=[O:17])=[O:16])[N:10]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[NH4+]>[OH:47][C@@H:26]([CH2:25][NH:24][CH2:23][CH2:22][C:21]1[CH:20]=[CH:19][C:18]([S:15]([CH2:14][C:11]2[N:10]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[O:13][N:12]=2)(=[O:17])=[O:16])=[CH:49][CH:48]=1)[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([CH3:46])[CH:30]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12044204HCID 12044204, compound

Product 1

HCID 12044205HCID 12044205, compoundYield 72.7%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the amino alcohol of Example 18(0.630 g, 0.887 mmol) in THF (12 mL) was added a 1M solution of TBAF (0.18 mL, 0.18 mmol). The reaction mixture was stirred for 6 h. TLC shows the absence of starting material, so 4 drops of a saturated aqueous ammonium chloride solution was added. The reaction mixture was evaporated in vacuo to dryness and the residue was flash chromatographed (silica gel; dichloromethane/chloroform/methanol: 5/4/1) to afford 0.357 g of the title compound as a white crystalline solid.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customchromatographed (silica gel; dichloromethane/chloroform/methanol: 5/4/1)

Sources & evidence

ORD record
ord-22c35452c006403b8e7049c106f11b8c
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

Loading…