Sodium hydride → ethyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)-phenyl carbonate

HRID 1776589ノート

反応式

HRID 1776589 の反応式
[C:1](=[O:19])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:7]=1)[O:2][CH2:3][CH3:4].[H-].[Na+].Cl.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>CN(C=O)C.C(Cl)Cl>[C:1](=[O:19])([O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N:14]([CH2:24][CH2:25][N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[S:15]([CH3:18])(=[O:16])=[O:17])[CH:7]=1)[O:2][CH2:3][CH3:4]

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86679540Ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonate

生成物 1

HCID 86679541ethyl 4-methoxy-3-(N-(2-morpholinoethyl)-methylsulfonamido)-phenyl carbonate収率 21.14%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
90 °C

実験手順

A solution of ethyl 4-methoxy-3-(methylsulfonamido)phenyl carbonate (0.850 g, 2.94 mmol) in dry DMF (15 ml) was cooled to 0° C. under nitrogen atmosphere, and sodium hydride (60% w/w, 0.300 g, 7.50 mmol) was added portion-wise. After 10 minutes, the cold bath was removed, 4-(2-chloroethyl)morpholine hydrochloride (0.680 mg, 3.65 mmol) was added, and the mixture was heated to 90° C. for 2 hours. After cooling to RT, the reaction mixture was diluted with DCM and washed with water. The organic layer was washed with brine and dried over Na2SO4; the solvent was evaporated and the crude was purified by flash chromatography on silica gel column (DCM:MeOH=10:0.1) affording ethyl 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)-phenyl carbonate (0.250 g, 0.621 mmol, 21.14% yield, UPLC-MS purity: 97%, MS/ESI+ 403.1 [MH]+).

後処理

  1. customthe cold bath was removed
  2. temperatureAfter cooling to RT
  3. washwashed with water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated
  7. customthe crude was purified by flash chromatography on silica gel column (DCM:MeOH=10:0.1)

出典と根拠

ORDレコード
ord-a4d1214d3fd24512aeacee0f5da23569
出典データセット
uspto-grants-2016_02
特許番号
US09265768B2

反応ノート

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