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 1532897ノート

反応式

HRID 1532897 の反応式
[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

参加物

5

反応物 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

生成物 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収率 51%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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 on 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) δ 9.56 (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), 1.45 (9H, s).

後処理

  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 on silica gel (2-5% methanol in CH2Cl2)

出典と根拠

ORDレコード
ord-c47de99236d74c33ac02a59c0d1a72ec
出典データセット
uspto-grants-2001_03
特許番号
US06204261B1

反応ノート

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