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1,2-Dichloroethane → 4-((S)-2-((S)-3-(3-(2-(tert-Butoxycarbonylamino)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide

HRID 520340
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HRID 520340 반응식
[C:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:17][CH2:16][S:15][C@H:14]2[C:18]([O:20][C@H:21]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:41])[F:40])=[C:34]([O:42][CH2:43][CH:44]3[CH2:46][CH2:45]3)[CH:33]=2)[CH2:22][C:23]2[C:28]([Cl:29])=[CH:27][N+:26]([O-:30])=[CH:25][C:24]=2[Cl:31])=[O:19])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.[NH2:47][CH2:48][CH2:49][NH:50][C:51](=[O:57])[O:52][C:53]([CH3:56])([CH3:55])[CH3:54].C(Cl)CCl>CN(C1C=CN=CC=1)C.CN(C=O)C.O>[C:53]([O:52][C:51]([NH:50][CH2:49][CH2:48][NH:47][C:1]([C:4]1[CH:5]=[C:6]([S:10]([N:13]2[CH2:17][CH2:16][S:15][C@H:14]2[C:18]([O:20][C@H:21]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH:39]([F:40])[F:41])=[C:34]([O:42][CH2:43][CH:44]3[CH2:46][CH2:45]3)[CH:33]=2)[CH2:22][C:23]2[C:24]([Cl:31])=[CH:25][N+:26]([O-:30])=[CH:27][C:28]=2[Cl:29])=[O:19])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)=[O:3])=[O:57])([CH3:56])([CH3:55])[CH3:54]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 111,2-DichloroethaneHCID 187201N-BOC-ethylenediamineHCID 710924964-((S)-2-((S)-3-(3-carboxyphenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide

생성물 1

HCID 1185584624-((S)-2-((S)-3-(3-(2-(tert-Butoxycarbonylamino)ethylcarbamoyl)phenylsulfonyl)-thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide
수율 88.1%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

4-((S)-2-((S)-3-(3-Carboxyphenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (200 mg, 0.278 mmol), tert-butyl 2-aminoethylcarbamate (89 mg, 0.556 mmol), DMAP (40.7 mg, 0.334 mmol) and EDC (160 mg, 0.834 mmol) were dissolved in DMF. The reaction was stirred at room temperature overnight to achieve completion. The reaction mixture was diluted with water, and the precipitate was washed with water, dissolved in ethyl acetate and extracted with HCl 1N, NaHCO3 5% and brine. The organic phase was dried over Na2SO4 and concentrated under vacuum to give 4-((S)-2-((S)-3-(3-(2-(tert-butoxycarbonylamino)ethylcarbamoyl)phenylsulfonyl)thiazolidine-2-carbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide (211 mg, 0.245 mmol, 88% yield).

후처리

  1. washthe precipitate was washed with water
  2. dissolutiondissolved in ethyl acetate
  3. extractionextracted with HCl 1N, NaHCO3 5% and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-0af03a1bab444088a2be031d1d14abaa
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09326976B2

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