Benzyl chloroformate → (2,6-Dimethyl-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester

HRID 905586

反応式

HRID 905586 の反応式
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH3:12][C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[C:15]([CH3:25])[C:14]=1[NH2:26].C(N(CC)C(C)C)(C)C>ClCCCl>[CH2:5]([O:4][C:2](=[O:3])[NH:26][C:14]1[C:15]([CH3:25])=[CH:16][C:17]([N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)=[CH:18][C:13]=1[CH3:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

5

反応物 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 230094142,6-Dimethyl-4-morpholin-4-yl-phenylamine

生成物 1

HCID 11508357(2,6-Dimethyl-4-morpholin-4-yl-phenyl)-carbamic acid benzyl ester収率 47%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Benzyl chloroformate (32 mg) was added to a solution of 0.15 M 2,6-dimethyl-4-morpholin-4-yl-phenylamine and 0.30 M N,N-diisopropyl-ethylamine in 1,2-dichloroethane (1 mL). The vial was shaken for 16 hours and concentrated in vacuo. Aqueous sodium hydroxide (1 M, 2 mL) was added and the crude mixture was extracted with isopropyl acetate/tetrahydrofuran (4:1, 2.5 mL). The organic phase was concentrated in vacuo and redissolved in dimethyl sulfoxide (0.5 mL) of which 0.2 mL was subjected to preparative LC-MS purification to furnish 9.5 mg (47% yield) of the title compound as an oil. LC-MS (m/z) 341 (MH+); tR=2.28, (UV, ELSD) 100%, 100%.

後処理

  1. concentrationconcentrated in vacuo
  2. additionAqueous sodium hydroxide (1 M, 2 mL) was added
  3. extractionthe crude mixture was extracted with isopropyl acetate/tetrahydrofuran (4:1, 2.5 mL)
  4. concentrationThe organic phase was concentrated in vacuo
  5. dissolutionredissolved in dimethyl sulfoxide (0.5 mL) of which 0.2 mL
  6. customwas subjected to preparative LC-MS purification

出典と根拠

ORDレコード
ord-9759227e99734243b73ec7539d960962
出典データセット
uspto-grants-2011_09
特許番号
US08012962B2

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