Potassium Iodide → Tert-butyl 3-(1-ethoxycarbonyl-3-cyclohexylpropyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

HRID 464865

반응식

HRID 464865 반응식
Cl.N[C@@H]1C(=O)NC2C=CC=CC=2OC1.C([O-])(=O)C.[Na+].C1(CCC(=O)C(OCC)=O)CCCCC1.[CH2:35]([O:37][C:38]([CH:40]([NH:49][CH:50]1[C:56](=[O:57])[NH:55][C:54]2[CH:58]=[CH:59][CH:60]=[CH:61][C:53]=2[O:52][CH2:51]1)[CH2:41][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:39])[CH3:36].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:69][C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71].[I-].[K+]>[Ni].O.C(OCC)(=O)C.CN(C)C=O.C(O)(=O)C.C(O)C>[CH2:35]([O:37][C:38]([CH:40]([NH:49][CH:50]1[C:56](=[O:57])[N:55]([CH2:69][C:70]([O:72][C:73]([CH3:76])([CH3:75])[CH3:74])=[O:71])[C:54]2[CH:58]=[CH:59][CH:60]=[CH:61][C:53]=2[O:52][CH2:51]1)[CH2:41][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)=[O:39])[CH3:36]

참가 물질

14

반응물 7

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 66052tert-Butyl chloroacetateHCID 517045Sodium AcetateHCID 13454680Ethyl 4-cyclohexyl-2-oxobutanoateHCID 18599716(S)-7-Amino-6,7-dihydro-9H-5-oxa-9-aza-benzocyclohepten-8-one hydrochlorideHCID 233200213-(1-Ethoxycarbonyl-3-cyclohexylpropyl)amino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one

생성물 1

HCID 23320010Tert-butyl 3-(1-ethoxycarbonyl-3-cyclohexylpropyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate

시약·촉매·용매 6

HCID 935Nickel촉매HCID 176Acetic Acid용매HCID 702Ethanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 3(S)-amino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one hydrochloride (2 g), ethanol (100 ml), sodium acetate (0.8 g), acetic acid (0.6 g), molecular sieves 4A (5 g) and ethyl 4-cyclohexyl-2-oxo-butyrate (5 g) is catalytically hydrogenated over Raney nickel at room temperature under atmospheric pressure. After the absorption of hydrogen ceases, the catalyst is removed by filtration and the filtrate is evaporated in vacuo. To the residue are added water (50 ml) and ethyl acetate (200 ml), and the mixture is agitated thoroughly. The ethyl acetate layer is dried over anhydrous magnesium sulfate and evaporated in vacuo to yield an oily residue containing 3-(1-ethoxycarbonyl-3-cyclohexylpropyl)amino-2,3,4,5-tetrahydro-1,5-benzoxazepine-4-one. A mixture of this oil, potassium carbonate (4 g), tert-butyl chloroacetate (3 g), potassium iodide (0.2 g) and N,N-dimethylformamide (20 ml) is stirred overnight at room temperature, and then diluted with a mixture of water (300 ml) and ethyl acetate (200 ml). The organic layer is separated, dried over anhydrous magnesium sulfate and evaporated in vacuo to yield an oil, which is purified by silica gel column chromatography using hexaneethyl acetate (4:1) as an eluant to yield tert-butyl 3-(1-ethoxycarbonyl-3-cyclohexylpropyl)amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetate (1 g) as a colorless oil.

후처리

  1. customAfter the absorption of hydrogen ceases
  2. customthe catalyst is removed by filtration
  3. customthe filtrate is evaporated in vacuo
  4. additionTo the residue are added water (50 ml) and ethyl acetate (200 ml)
  5. dry with materialThe ethyl acetate layer is dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. customto yield an oily residue
  8. stirringis stirred overnight at room temperature
  9. customThe organic layer is separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated in vacuo
  12. customto yield an oil, which
  13. customis purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8fb58d5fd0f240138c03f62b9c7de446
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04548932

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