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Benzyl chloroformate → (1S,9S)-tert-butyl 9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

HRID 1711950
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HRID 1711950 반응식
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@@H:13]1[C:19](=[O:20])[N:18]2[C@H:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22][CH2:23][CH2:24][N:17]2[C:16](=[O:32])[CH2:15][CH2:14]1.C([O-])(O)=O.[Na+].O1CCOCC1>CCOC(C)=O.O>[CH2:5]([O:4][C:2]([NH:12][C@@H:13]1[C:19](=[O:20])[N:18]2[C@H:21]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:22][CH2:23][CH2:24][N:17]2[C:16](=[O:32])[CH2:15][CH2:14]1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
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HCID 10387Benzyl chloroformateHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 15434568tert-Butyl (1S,9S)-9-amino-6,10-dioxooctahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate

생성물 1

HCID 67022104(1S,9S)-tert-butyl 9-(benzyloxycarbonylamino)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate수율 88.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Benzyl chloroformate (1.07 g) was added dropwise to a stirred ice cold mixture of the (1S,9S) t-butyl 9-amino-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino[1,2-a][1,2]diazepine-1-carboxylate (GB 2,128,984; 1.55 g, 5.21 mmol), NaHCO3 (0.66 g, 7.82 mmol), dioxan (32 ml) and water (8 ml). The mixture was kept at 5° C. for 15 min then for 2 h at room temperature. The mixture was diluted with EtOAc (50 ml), washed twice with sat. NaHCO3 solution, dried (MgSO4) and concentrated. The oily residue was purified by flash chromatography to afford 211d (1.98 g, 88%) of a colourless oil: [α]D24 −56.4 (c 1.0, CH2Cl2); IR (thin film) 3325, 2979, 2946, 1728, 1677, 1528, 1456, 1422, 1370, 1340, 1272, 1245, 1156, 1122, 1056, 916, 734, 699; 1H NMR (CDCl3) δ 7.29 (5H, m), 5.81-5.72 (1H, m), 5.26-5.20 (1H, m), 5.05 (2H, s), 4.69-4.51 (2H, m), 3.48-3.36 (1H, m), 2.81-2.51 (2H, m), 2.34-2.19 (2H, m), 1.90-1.54 (4H, m), 1.41 (9H, s); Anal. Calcd for C22H29N3O6.H2O: C, 58.79; H, 6.92; N, 9.35. Found: C, 59.10; H, 6.57; N, 9.25. MS (ES+) 454 (M++Na, 87%), 432 (M++1, 100).

후처리

  1. waitfor 2 h at room temperature
  2. washwashed twice with sat. NaHCO3 solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe oily residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-2f459887290f43de9de126538475816e
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07790713B2

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