Heptane → methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate

HRID 264329노트

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HRID 264329 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH3:24]CCCCCC>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C@H:13]([CH:14]([CH3:16])[CH3:15])[C:17]([O:19][CH3:24])=[O:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 8900HeptaneHCID 24386Thionyl ChlorideHCID 1133588N-[4-methoxybenzenesulfonyl]-(D)-valine

생성물 1

HCID 10946547methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

반응 조건

온도
5 °C

실험 절차

To a solution of N-[4-methoxybenzenesulfonyl]-(D)-valine (8369 g, 29.13 mol) in methanol (30 L) at 5° C. is added thionyl chloride (2176 mL, 29.7 mol) over 2.5 hours. After stirring for 3 hours at 5° C., the reaction is stirred for 36 hours at room temperature. Most of the solvent is evaporated, and the crude product is dissolved in toluene (80 L). The toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L), dried (Na2SO4), and the solvent is evaporated. The solid obtained is dissolved in ethyl acetate (8 L) and heptane (16 L) is added to induce crystallization. The precipitated product is collected by filtration to provide methyl 2(R)-[[4-methoxybenzenesulfonyl]amino]-3-methylbutanoate.

후처리

  1. stirringthe reaction is stirred for 36 hours at room temperature
  2. customMost of the solvent is evaporated
  3. dissolutionthe crude product is dissolved in toluene (80 L)
  4. washThe toluene layer is then washed with water (20 L), saturated sodium bicarbonate (20 L), water again (20 L), 2N hydrochloric acid (20 L), brine (20 L)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent is evaporated
  7. customThe solid obtained
  8. customcrystallization
  9. filtrationThe precipitated product is collected by filtration

출처 및 근거

ORD 기록
ord-ba04457198e54793b702012d62934ded
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646167

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