Methyl Isocyanate → (1-{1-[6-(3,4-Difluoro-phenoxy)-4-methylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

HRID 1965184ノート

反応式

HRID 1965184 の反応式
[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:12]([C:14](=[O:40])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[NH:28][CH2:29][CH:30]([O:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=3)[CH:24]12)=[O:22])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:51][N:52]=[C:53]=[O:54]>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:12]([C:14](=[O:40])[NH:15][CH:16]([C:21]([N:23]1[CH2:27][CH2:26][CH:25]2[N:28]([C:53](=[O:54])[NH:52][CH3:51])[CH2:29][CH:30]([O:31][C:32]3[CH:37]=[CH:36][C:35]([F:38])=[C:34]([F:39])[CH:33]=3)[CH:24]12)=[O:22])[C:17]([CH3:19])([CH3:18])[CH3:20])[CH3:13])[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 67606709(1-{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester

生成物 1

HCID 67606741(1-{1-[6-(3,4-Difluoro-phenoxy)-4-methylcarbamoyl-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propylcarbamoyl}-ethyl)-methyl-carbamic acid benzyl ester収率 91.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution containing 35 (228 mg, 0.4 mmol), DIPEA (104 mg, 0.8 mmol) in DCM (5 mL) was cooled to 0° C. Methyl isocyanate (35 mg, 0.6 mmol) was added. After 3 h, the reaction mixture was warmed to ambient temperature, diluted with DCM, washed successively with saturated aqueous NaHCO3, 1N HCl, and brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford the crude 40 (230 mg) which was used without further purification. Mass spectrum, m/z [630.1] (M+H)+.

後処理

  1. temperaturethe reaction mixture was warmed to ambient temperature
  2. washwashed successively with saturated aqueous NaHCO3, 1N HCl, and brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-5664a35799a94ba2919cd82fd5db0a2a
出典データセット
uspto-grants-2013_04
特許番号
US08415486B2

反応ノート

読み込み中…