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 1524268ノート

反応式

HRID 1524268 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8dfcce4ca54a4051b1ea1d03f75b011b
出典データセット
uspto-grants-2015_07
特許番号
US09079880B2

反応ノート

読み込み中…