3-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acid → ((S)-2-{3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester

HRID 1524268노트

반응식

HRID 1524268 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]1[CH2:17][CH2:16][C:11]2[N:12]=[C:13]([NH2:15])[S:14][C:10]=2[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:19]([C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([CH2:30][O:31][C:32]2[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=2)[C:35](O)=[O:36])=[O:29])=[CH:23][CH:22]=1)#[N:20]>CN(C)C(=O)C.O>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]1[CH2:17][CH2:16][C:11]2[N:12]=[C:13]([NH:15][C:35](=[O:36])[C:34]3[CH:38]=[CH:39][CH:40]=[C:32]([O:31][CH2:30][C:28](=[O:29])[NH:27][C:24]4[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[CH:22][CH:23]=4)[CH:33]=3)[S:14][C:10]=2[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 454173003-[(4-Cyano-phenylcarbamoyl)-methoxy]-benzoic acidHCID 49844272tert-butyl N-[(6S)-2-amino-4,5,6,7-tetrahydro-1,3-benzothiazol-6-yl]carbamate

생성물 1

HCID 86667841((S)-2-{3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester수율 75.2%

시약·촉매·용매 2

HCID 962Water용매HCID 31374Dimethylacetamide용매

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온도
50 °C

실험 절차

Add ((S)-2-amino-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester (0.10 g, 0.37 mmol) followed by O-(7-aza-benzotriazole-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate (0.13 g, 0.34 mmol) and N,N-diisopropylethyl (0.13 mL, 0.70 mmol) amine to a solution of 3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoic acid (0.10 g, 0.34 mmol) in N,N-dimethylacetamide (3 mL). Heat the mixture to 50° C. for 2 h then cool to room temperature and dilute with water causing a solid to precipitate from solution. Collect the light yellow solid by filtration, wash with water, and dry on the filter pad to provide 0.14 g of ((S)-2-{3-[(4-cyano-phenylcarbamoyl)-methoxy]-benzoylamino}-4,5,6,7-tetrahydro-benzothiazol-6-yl)-carbamic acid tert-butyl ester.

후처리

  1. temperaturethen cool to room temperature
  2. customto precipitate from solution
  3. customCollect the light yellow solid
  4. filtrationby filtration
  5. washwash with water
  6. customdry on the filter pad

출처 및 근거

ORD 기록
ord-8dfcce4ca54a4051b1ea1d03f75b011b
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079880B2

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