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Water → HCID 86663798, 화합물

HRID 2370605
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HRID 2370605 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:19](=[O:20])[C:15]3([CH2:18][CH2:17][CH2:16]3)[NH:14][C:13]2=[O:21])=[CH:8][C:7]=1[C:22]([F:25])([F:24])[F:23])([O-:5])=[O:4].CS(O[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:48])([F:47])[F:46])(=O)=O.O>CN(C=O)C>[N+:3]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:19](=[O:20])[C:15]3([CH2:16][CH2:17][CH2:18]3)[N:14]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][S:40][CH2:41][CH2:42][CH2:43][C:44]([F:50])([F:49])[C:45]([F:46])([F:47])[F:48])[C:13]2=[O:21])=[CH:8][C:7]=1[C:22]([F:25])([F:24])[F:23])([O-:5])=[O:4]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 58899364HCID 58899364, 화합물HCID 66750519HCID 66750519, 화합물

생성물 1

HCID 86663798HCID 86663798, 화합물수율 33%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
23 °C

실험 절차

NaH (to 60%) (44 mg, 1.1 mmole) is added under argon to a solution of 7-[4-nitro-3-(trifluoromethyl)phenyl]-5,7-diazaspiro[3.4]octane-6,8-dione (329 mg, 1 mmole) in anhydrous DMF (9 ml). A release of gas accompanies the change in colour of the reaction medium which becomes orange. Stirring is maintained for 1 hour at 23° C. before adding 9-[(4,4,5,5,5-pentafluoropentyl)-thio]nonyl methanesulphonate (prepared according to an experimental protocol described in WO 2005077968) (332 mg, 0.8 mmole). After reaction for 15 hours, the reaction medium is poured into water (25 ml) and extracted with AcOEt (2×25 ml). The organic phases are combined and washed successively with water (25 ml) and salt water (25 ml). After drying over Na2SO4, the organic solution is filtered and concentrated under vacuum. The evaporation residue is purified on an RP18 silica column (eluent: ACN/H2O: 8/2 to 100). The expected compound is obtained in the form of a colourless oil with a yield of 33% (214 mg).

후처리

  1. customprepared
  2. customAfter reaction for 15 hours
  3. extractionextracted with AcOEt (2×25 ml)
  4. washwashed successively with water (25 ml) and salt water (25 ml)
  5. dry with materialAfter drying over Na2SO4
  6. filtrationthe organic solution is filtered
  7. concentrationconcentrated under vacuum
  8. customThe evaporation residue is purified on an RP18 silica column (eluent: ACN/H2O: 8/2 to 100)

출처 및 근거

ORD 기록
ord-475a2166cd01431595ff476aa7c2905b
출처 데이터셋
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08710091B2

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