Hydrochloric Acid → t-Butyl 4-[9-(benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino-[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoate

HRID 2230454노트

반응식

HRID 2230454 반응식
[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]([CH:39]=[O:40])[CH2:26][CH2:27][C:28](=NNC(N)=O)[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:41])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=[O:43].Cl>CO>[C:1]([NH:9][CH:10]1[C:16](=[O:17])[N:15]2[CH:18]([C:22]([NH:24][CH:25]([CH:39]=[O:40])[CH2:26][CH2:27][C:28]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:43])=[O:23])[CH2:19][CH2:20][CH2:21][N:14]2[C:13](=[O:41])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 53703560t-Butyl 4-[9-(benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino-[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoate semicarbazone

생성물 1

HCID 54215480t-Butyl 4-[9-(benzoylamino)-6,10-dioxo-1,2,3,4,7,8,9,10-octahydro-6H-pyridazino-[1,2-a][1,2]diazepine-1-carboxamido]-5-oxopentanoate

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of semicarbazone 233e (390 mg, 0.68 mmol) in methanol (10 ml) was cooled at 0° C. and then treated with a 38% aq. solution of formaldehyde (2 ml) and 1M HCl (2 ml). The reaction mixture was then stirred overnight at room temperature. The solution was concentrated to remove the methanol. The aq. solution was extracted with EtOAc (30 ml). The organic solution was successively washed with 10% NaHCO3 (30 ml) and sat. aq. NaCl (30 ml), dried (MgSO4) and concentrated. Purification by flash chromatography or silica gel (2-5% methanol in CH2Cl2) afforded 234e (179 mg, 51% as a white foam: [α]D20 −101° (c 0.064, MeOH; IR (KBr)3346, 2976, 2934, 1730, 1657, 1535, 1456, 1425, 1278, 1255, 1156, 708; 1H NMR (CDCl3) δ9.56 (1H, s), 7.88-7.38 (5H, m), 7.01 and 6.92 (2H, 2d) 5.27-5.08 (2H, m), 4.69-4.46 (1H, m), 3.50-3.27 (2H, m), 3.15-2.73 (2H, m), 2.46-1.83 (10H, m), 1.43 (9H, s).

후처리

  1. concentrationThe solution was concentrated
  2. customto remove the methanol
  3. extractionThe aq. solution was extracted with EtOAc (30 ml)
  4. washThe organic solution was successively washed with 10% NaHCO3 (30 ml) and sat. aq. NaCl (30 ml)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography or silica gel (2-5% methanol in CH2Cl2)

출처 및 근거

ORD 기록
ord-88715b85829046cd890d98cf09e37520
출처 데이터셋
uspto-grants-2002_07
특허 번호
US06423840B1

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