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Water → 3,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester

HRID 1912419
노트
인쇄 미리보기

반응식

HRID 1912419 반응식
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][C:12]([NH:25][C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])([C:16]([F:24])([F:23])[CH2:17]OS(C)(=O)=O)[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][C:12]2([N:25]([C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[O:27])[CH2:17][C:16]2([F:24])[F:23])[CH2:11]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]
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참가 물질

5

반응물 3

HCID 962WaterHCID 24758Sodium hydrideHCID 582933543-Benzyloxycarbonylamino-3-(1,1-difluoro-2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 582933383,3-Difluoro-1,6-diaza-spiro[3.5]nonane-1,6-dicarboxylic acid 1-benzyl ester 6-tert-butyl ester수율 91.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
0 °C

실험 절차

To a suspension of sodium hydride (1.7 g, with 40% mineral oil) in N,N-dimethylformamide (428 ml) cooled to 0° C. was added a solution of an optically-active compound of 3-benzyloxycarbonylamino-3-(1,1-difluoro-2-methanesulfonyloxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (17.1 g) in N,N-dimethylformamide (86 ml), and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The separated organic layer was sequentially washed with water and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1) to give the titled compound (12.6 g).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe separated organic layer was sequentially washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-5ff145eff7ea4a6a8467e06774bfa630
출처 데이터셋
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08609647B2

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