1-Methylimidazole → HCID 178523396、化合物

HRID 1396878ノート

反応式

HRID 1396878 の反応式
[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:8]([N:10]2[C@H:14]([C:15]([OH:17])=O)[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.CN1C=CN=C1.S(Cl)(C)(=O)=O.[NH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][N+:53]=1[O-:58]>CN(C=O)C>[CH:1]1([CH2:6][C@H:7]([CH2:28][N:29]([CH:38]=[O:39])[O:30][CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:8]([N:10]2[C@H:14]([C:15]([NH:51][C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][N+:53]=3[O-:58])=[O:17])[CH2:13][CH2:12][N:11]2[C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:19])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 13901-MethylimidazoleHCID 31297Methanesulfonyl chlorideHCID 86706346(3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acidHCID 178507601HCID 178507601、化合物

生成物 1

HCID 178523396HCID 178523396、化合物収率 51.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of (3S)-2-[(2R)-3-cyclopentyl-2-({formyl[(phenylmethyl)oxy]amino}methyl)propanoyl]-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidine carboxylic acid (176 mg, 0.327 mmol) in DMF (2 ml) was added 1-methylimidazole (52 μl, 0.655 mmol) and cooled to 0° C. Mesyl chloride (27 μL, 0.344 mmol) was added dropwise at 0° C., and the resulting mixture was stirred for 30 min followed by the addition of 2-amino pyridine N-oxide (36 mg, 0.327 mmol). The reaction was warmed to rt. After 2 h, the reaction mixture was concentrated, diluted with methanol, and purified by reverse phase HPLC to afford 105 mg (0.167 mmol, 51%) of the title compound. LC/MS: (M+H)+: 629.8.

後処理

  1. temperatureThe reaction was warmed to rt
  2. waitAfter 2 h
  3. concentrationthe reaction mixture was concentrated
  4. additiondiluted with methanol
  5. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-dcf1187568b94db88d5615ca40736924
出典データセット
uspto-grants-2014_12
特許番号
US08901119B2

反応ノート

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