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 1592040노트

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HRID 1592040 반응식
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

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxide2회HCID 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

생성물 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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-90f1b7030d6240f79ed0d26ff0488e32
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07291635B2

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