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 1592040Notes

Reaction equation

HRID 1592040 reaction equation
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

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxide2×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

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-90f1b7030d6240f79ed0d26ff0488e32
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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