Water → [4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester

HRID 23582ノート

反応式

HRID 23582 の反応式
[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[S:21](Cl)(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.O>O1CCCC1>[CH2:1]([O:8][C:9](=[O:25])[CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[CH:13][C:12]=1[S:21]([N:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1)(=[O:23])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 8083MorpholineHCID 8471TriethylamineHCID 86594678HCID 86594678、化合物

生成物 1

HCID 69732356[4,5-Dimethoxy-2-(morpholine-4-sulfonyl)-phenyl]-acetic acid benzyl ester収率 60.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a stirred mixture of (2-chlorosulfonyl-4,5-dimethoxy-phenyl)-acetic acid benzyl ester (15.0 g, 39.0 mmol) in anhydrous tetrahydrofuran (45 cm3) cooled to 0° C. in an ice bath under an atmosphere of dry nitrogen was added triethylamine (6.00 cm3, 43 mmol). The mixture was stirred 2 minutes and morpholine (3.75 cm3, 43 mmol) was added dropwise to form a solid mass. To efficiently stir the mixture additional anhydrous tetrahydrofuran (145 cm3) was added and the mixture was warmed to ambient temperature over 20 hours. Water was added to the mixture and extracted with ethyl acetate (2×100 cm3). The combined ethyl acetate extracts were dried over sodium sulfate, vacuum filtered and the filtrate volatile fractions removed in vacuo to afford a crude tan solid. The crude solid was recrystallized from toluene (150 cm3) to afford the title compound as tan crystals (10.2 g, 60.2%) with a positive ion ESI (M+H)+436.2.

後処理

  1. customto form a solid mass
  2. additionwas added
  3. temperaturethe mixture was warmed to ambient temperature over 20 hours
  4. extractionextracted with ethyl acetate (2×100 cm3)
  5. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate, vacuum
  6. filtrationfiltered
  7. customthe filtrate volatile fractions removed in vacuo
  8. customto afford a crude tan solid
  9. customThe crude solid was recrystallized from toluene (150 cm3)

出典と根拠

ORDレコード
ord-1d10b31161ba47608dd5f6a1f763fcbb
出典データセット
uspto-grants-2005_02
特許番号
US06852713B2

反応ノート

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