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Tetrabutylammonium Fluoride → (2S)-4-(3-{2-[4-(5-tert-Butyl-[1,2,4]oxadiazol-3-ylmethylsulfanyl)-phenyl]-ethylamino}-2-hydroxy-propoxy)-phenol

HRID 990088
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HRID 990088 반응식
[Si]([O:18][C:19]1[CH:49]=[CH:48][C:22]([O:23][CH2:24][C@@H:25]([OH:47])[CH2:26][NH:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([S:36][CH2:37][C:38]3[N:42]=[C:41]([C:43]([CH3:46])([CH3:45])[CH3:44])[O:40][N:39]=3)=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[NH4+]>[C:43]([C:41]1[O:40][N:39]=[C:38]([CH2:37][S:36][C:33]2[CH:32]=[CH:31][C:30]([CH2:29][CH2:28][NH:27][CH2:26][C@H:25]([OH:47])[CH2:24][O:23][C:22]3[CH:48]=[CH:49][C:19]([OH:18])=[CH:20][CH:21]=3)=[CH:35][CH:34]=2)[N:42]=1)([CH3:46])([CH3:44])[CH3:45]
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참가 물질

5

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 59886865(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfanyl)phenethyl]amino}-2-propanol

생성물 1

HCID 10276164(2S)-4-(3-{2-[4-(5-tert-Butyl-[1,2,4]oxadiazol-3-ylmethylsulfanyl)-phenyl]-ethylamino}-2-hydroxy-propoxy)-phenol수율 100%

시약·촉매·용매 2

HCID 25517Ammonium Chloride
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the amino alcohol of Example 31(0.140 g, 0.201 mmol) in THF (3 mL) was added a 1M solution of TBAF (0.10 mL, 0.10 mmol). The reaction mixture was stirred for 6 h. TLC showed the absence of starting material, therefore 2 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: 15/5/3) to afford 0.092 g of the title compound as a tan foam.

후처리

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customchromatographed (silica gel; dichloromethane/chloroform/methanol: 15/5/3)

출처 및 근거

ORD 기록
ord-20064ff24c3f4bcb86e59ab74ec63268
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06458817B1

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