Sodium hydride → [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-{2-[(E)-2-(-4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester

HRID 1271439노트

반응식

HRID 1271439 반응식
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:27][C:28]1[N:29]=[C:30]([CH:33]=[CH:34][C:35]2[CH:40]=[CH:39][C:38]([S:41]([C:43]([F:46])([F:45])[F:44])=[O:42])=[CH:37][CH:36]=2)[O:31][CH:32]=1.[Cl-].[NH4+]>CN(C)C=O>[C:1]([O:5][C:6](=[O:23])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][N:18]2[CH:22]=[CH:21][N:20]=[N:19]2)=[CH:10][CH:9]=1)[CH2:27][C:28]1[N:29]=[C:30](/[CH:33]=[CH:34]/[C:35]2[CH:36]=[CH:37][C:38]([S:41]([C:43]([F:46])([F:44])[F:45])=[O:42])=[CH:39][CH:40]=2)[O:31][CH:32]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 69220256[4-(4-[1,2,3]Triazol-1-yl-butyl)phenyl]-carbamic acid tert-butyl esterHCID 692923894-Chloromethyl-2-[2-(4-trifluoromethylsulfinyl-phenyl)-vinyl]-oxazole

생성물 1

HCID 69487104[4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-{2-[(E)-2-(-4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester수율 29%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an ice-cold solution of [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-carbamic acid tert-butyl ester (188 mg, 0.6 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydride (16.5 mg, 0.65 mmol) and the mixture stirred for 30 min. After addition of 4-chloromethyl-2-[2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazole (200 mg, 0.6 mmol), the mixture was stirred at room temperature over night, then mixed with 40 ml ammonium chloride solution, thoroughly extracted with ethyl acetate and the extract dried and evaporated. Flash column chromatography (ethyl acetate/heptane 2:1) yielded 105 mg (29%) [4-(4-[1,2,3]triazol-1-yl-butyl)phenyl]-{2-[(E)-2-(−4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-carbamic acid tert-butyl ester as oily residue.

후처리

  1. stirringthe mixture was stirred at room temperature over night
  2. extractionthoroughly extracted with ethyl acetate
  3. customthe extract dried
  4. customevaporated

출처 및 근거

ORD 기록
ord-9f3ffb4bb877405aa6dbf53b816f1601
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205326B2

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