Potassium tert-butoxide → 3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

HRID 1592040ノート

反応式

HRID 1592040 の反応式
C([O:3][C:4](=O)[CH2:5][N:6]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH:18]2[NH:24][C:23](=[O:25])[C:22]3[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=3[NH:20][C:19]2=[O:30])=[CH:13][C:12]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[S:7]([NH2:10])(=[O:9])=[O:8])C.CC(C)([O-])C.[K+]>C1COCC1>[CH2:32]([O:31][C:12]1[CH:13]=[C:14]([CH:15]=[CH:16][C:11]=1[N:6]1[CH2:5][C:4](=[O:3])[NH:10][S:7]1(=[O:8])=[O:9])[CH2:17][CH:18]1[NH:24][C:23](=[O:25])[C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[NH:20][C:19]1=[O:30])[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

参加物

4

反応物 2

HCID 23665647Potassium tert-butoxide2 回HCID 67138957N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester

生成物 1

HCID 671383483-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of the title N compound, N-[2-benzyloxy-4-(2,5-dioxo-2,3,4,5-tetrahydro-1H-benzo[1,4]diazepin-3-ylmethyl)-phenyl]-N-[aminosulfonyl]-amino-acetic acid ethyl ester (93 mg, 0.168 mmol) in THF is cooled to 0° C. and treated dropwise with a solution of potassium t-butoxide in THF (1M, 0.244 mL, 0.244 mmol). After stirring at 0° C. for 30 min, additional potassium t-butoxide solution is added and stirring continued for another 1 h. The resulting suspension of fine solids is centrifuged, the supernatant is decanted and the cake of solids is suspended in EtOAc and centrifuged. The supernatant is decanted and the cake of solids is triturated with EtOAc and 2N aqueous HCl. The EtOAc layer is washed with brine, dried over anhydrous MgSO4, decolorized with charcoal, filtered and evaporated to give 3-[3-benzyloxy-4-(1,1,4-trioxo-[1,2,5]thiadiazolidin-2-yl)-benzyl]-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione as a foam: [M+1]+=507.

後処理

  1. stirringstirring
  2. waitcontinued for another 1 h
  3. additionThe resulting suspension of fine solids
  4. customthe supernatant is decanted
  5. customThe supernatant is decanted
  6. customthe cake of solids is triturated with EtOAc and 2N aqueous HCl
  7. washThe EtOAc layer is washed with brine
  8. dry with materialdried over anhydrous MgSO4
  9. filtrationfiltered
  10. customevaporated

出典と根拠

ORDレコード
ord-90f1b7030d6240f79ed0d26ff0488e32
出典データセット
uspto-grants-2007_11
特許番号
US07291635B2

反応ノート

読み込み中…