Triethylamine → Dimethyl 3-(2-methanesulfonylethylamino)-2-pentenedioate

HRID 231890ノート

反応式

HRID 231890 の反応式
O[CH2:2][CH2:3][NH:4][C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][C:7]([O:9][CH3:10])=[O:8].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>O>[CH3:23][S:24]([CH2:2][CH2:3][NH:4][C:5]([CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:6][C:7]([O:9][CH3:10])=[O:8])(=[O:26])=[O:25]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2 回HCID 74015716Dimethyl 3-(2-hydroxyethylamino)-2-pentenedioate

生成物 1

HCID 74015715Dimethyl 3-(2-methanesulfonylethylamino)-2-pentenedioate収率 93%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

The solution of dimethyl 3-(2-hydroxyethylamino)-2-pentenedioate was cooled to 0° C., and triethylamine (235 mL, 170.6 g, 1.69 mol) was added in one portion. Methanesulfonyl chloride (168.8 g, 1.47 mol) was added dropwise via an addition funnel over 3.75 hours, with the temperature rising to 5°-7° C. The medium-yellow slurry darkened to yellow-orange as the last 10 mL methanesulfonyl chloride was added. The mixture was stirred at 0° C. for an additional 2 hours, and water (250 mL) added. The organic phase was washed with water (4×500 mL) and brine (250 mL), and dried overnight over anhydrous magnesium sulfate. After filtration, the solvents were evaporated on a rotary evaporator under reduced pressure at 50° C. to afford 310.0 g (93% yield) of dimethyl 3-(2-methanesulfonylethylamino)-2-pentenedioate as a red oil. The mesylenamine may be purified at this point, if necessary or desired, and may be converted to the haloenamine by the following method or used directly in Step 2, Alternate II.

後処理

  1. customrising to 5°-7° C
  2. additionwas added
  3. washThe organic phase was washed with water (4×500 mL) and brine (250 mL)
  4. dry with materialdried overnight over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvents were evaporated on a rotary evaporator under reduced pressure at 50° C.

出典と根拠

ORDレコード
ord-5047f2d4ab0144dab7a29229f3512c1e
出典データセット
uspto-grants-1989_07
特許番号
US04849526

反応ノート

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