Sodium Bicarbonate → tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate

HRID 1807747노트

반응식

HRID 1807747 반응식
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:29])([F:31])[F:30]

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

생성물 1

HCID 86638560tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate수율 63.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of tert-butyl 1,4-diazepane-1-carboxylate (24.52 mmol, 4.91 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (24.52 mmol, 8.26 g) and sodium hydrogencarbonate (36.8 mmol, 3.09 g) in acetonitrile (100 mL) was stirred for 24 hours then was concentrated under reduced pressure. Dichloromethane was added and the suspension was filtered. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%) to give the title compound (7.1 g). MS (ESI) m/z 457.2 [M+H]+

후처리

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%)

출처 및 근거

ORD 기록
ord-3c9b728cc4a94539b578c54ab3790306
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08357679B2

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