N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate

HRID 915016

反応式

HRID 915016 の反応式
Cl.[NH2:2][CH:3]([C:12]1[CH:13]=[CH:14][C:15](=[O:21])[N:16]([CH:18]([CH3:20])[CH3:19])[N:17]=1)[C:4](=[O:11])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O=C1CCC(=O)N1[O:29][C:30](=O)[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH:18]([N:16]1[C:15](=[O:21])[CH:14]=[CH:13][C:12]([CH:3]([NH:2][C:30](=[O:29])[CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:37])[CH3:38])[C:4](=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)=[N:17]1)([CH3:19])[CH3:20]

参加物

5

反応物 3

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 81531DiisopropylethylamineHCID 69331476HCID 69331476、化合物

生成物 1

HCID 86600908Tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate収率 81.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
22.5 °C

実験手順

Under ice-cooling, to a suspension of 6-(1-amino-2-oxo-2-phenylethyl)-2-isopropyl-3(2H)-pyridazinone hydrochloride (1.00 g) and tert-butyl {2-[(2,5-dioxo-1-pyrrolidinyl)oxy]-2-oxoethyl}carbamate (973 mg) in CH2Cl2 (10 ml) was added ethyl(diisopropyl)amine (0.651 ml) and stirred at the same temperature for 2 hours and at 20-25° C. for 18 hours. The mixture was washed with water, dried over MgSO4 and concentrated under reduced pressure to give syrup. The syrup was purified by column chromatography on silica gel (EtOAc only) to give tert-butyl (2-{[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}-2-oxoethyl)carbamate as an amorphous solid (1.13 g).

後処理

  1. washThe mixture was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give syrup
  5. customThe syrup was purified by column chromatography on silica gel (EtOAc only)

出典と根拠

ORDレコード
ord-24b84654b7be4e2794f1aad9976c8871
出典データセット
uspto-grants-2007_09
特許番号
US07265120B2

関連ノート

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