Water → HCID 59619202, 화합물

HRID 1367552노트

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HRID 1367552 반응식
[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:16])=[O:15])[CH2:11][C@H:10]2[CH2:25][O:26]CC2C=CC(OC)=CC=2)=[O:8])[CH2:5][CH2:4]1)#[N:2].O>ClCCl>[C:1]([C:3]1([NH:6][C:7]([C@@H:9]2[CH2:13][C@@H:12]([S:14]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[Cl:24])(=[O:15])=[O:16])[CH2:11][C@H:10]2[CH2:25][OH:26])=[O:8])[CH2:5][CH2:4]1)#[N:2]

참가 물질

4

반응물 2

HCID 962WaterHCID 59619362HCID 59619362, 화합물

생성물 1

HCID 59619202HCID 59619202, 화합물수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a cold mixture of (1R,2R,4S)-4-(2-Chloro-4-fluoro-benzenesulfonyl)-2-(4-methoxy-benzyloxymethyl)-cyclopentanecarboxylic acid (1-cyano-cyclopropyl)-amide (example 153, step 9, 171 mg) in dichloromethane (4 mL) was added water (0.2 mL) and dichlorodicyanoquinone (97 mg). The reaction mixture was stirred 90 min at room temperature. The suspension was filtered and the solid was washed with dichloromethane. The resulting liquor was partionned between dichloromethane and saturated aqueous solution of sodium hydrogenocarbonate. The aqueous layer was washed with dichloromethane. The combined organic layers were washed brine, dried over sodium sulfate, filtered and evaporated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant to afford the title compound (101 mg, 77%) as a white solid. MS (EI): 401.1 (M+H)+.

후처리

  1. filtrationThe suspension was filtered
  2. washthe solid was washed with dichloromethane
  3. washThe aqueous layer was washed with dichloromethane
  4. washThe combined organic layers were washed brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel with a gradient of dichlormethane:methanol (98:2 to 19:1 v/v) as eluant

출처 및 근거

ORD 기록
ord-1b258d13f53a49a79c6550722476dabb
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893099B2

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