Tetrabutylammonium Fluoride → 4-({(2S)-3-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-2-hydroxypropyl}oxy)phenol

HRID 990081Notes

Reaction equation

HRID 990081 reaction equation
[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:53]=[CH:52][C:19]([CH2:20][CH2:21][NH:22][CH2:23][C@H:24]([OH:51])[CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)=[CH:29][CH:28]=3)=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[NH4+]>[CH2:1]([C:8]1[O:12][N:11]=[C:10]([CH2:13][S:14]([C:16]2[CH:53]=[CH:52][C:19]([CH2:20][CH2:21][NH:22][CH2:23][C@H:24]([OH:51])[CH2:25][O:26][C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)=[CH:18][CH:17]=2)=[O:15])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 12044209(2S)-1-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-3-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-2-propanol

Product 1

HCID 120442104-({(2S)-3-[(4-{[(5-benzyl-1,2,4-oxadiazol-3-yl)methyl]sulfinyl}phenethyl)amino]-2-hydroxypropyl}oxy)phenolYield 64.6%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the amino alcohol of Example 23 (0.490 g, 0.643 mmol) in THF (10 mL) was added a 1M solution of TBAF (0.13 mL, 0.13 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: 5/4/1) to afford 0.211 g of the title compound as a white crystalline solid. MP=51-57° C.

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-fa003001e4b24927ae8c484fdd1ade6f
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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