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

HRID 2108213노트

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HRID 2108213 반응식
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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2회HCID 74015716Dimethyl 3-(2-hydroxyethylamino)-2-pentenedioate

생성물 1

HCID 74015715Dimethyl 3-(2-methanesulfonylethylamino)-2-pentenedioate수율 93%

시약·촉매·용매 1

HCID 962Water용매

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온도
0 °C

실험 절차

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.

후처리

  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.

출처 및 근거

ORD 기록
ord-e161b0e2a6f04625801e08263e55b431
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937368

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