Tetrabutylammonium Fluoride → 4[((2S)-2-hydroxy-3-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}propyl)oxy]phenol

HRID 990086Notes

Reaction equation

HRID 990086 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:48]=[CH:47][C:21]([CH2:22][CH2:23][NH:24][CH2:25][C@H:26]([OH:46])[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)=[CH:31][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:46][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:48][CH:47]=1)[CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 70137905(2S)-1-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-3-{4-[(triisopropylsilyl)oxy]phenoxy}-2-propanol

Product 1

HCID 233890764[((2S)-2-hydroxy-3-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}propyl)oxy]phenolYield 60.7%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the amino alcohol of Example 28(0.57 g, 0.733 mmol) in THF (11 mL) was added a 1M solution of TBAF (0.15 mL, 0.15 mmol). The reaction mixture was stirred for 6 h. TLC shows the absence of starting material, so 3 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: 6/3/1) to afford 0.240 g of the title compound as a white foam.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customchromatographed (silica gel; dichloromethane/chloroform/methanol: 6/3/1)

Sources & evidence

ORD record
ord-78d37ce0b0524d6680e767e97f2a3458
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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