Triethylamine → Methyl 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-oxopentanoate

HRID 1737939노트

반응식

HRID 1737939 반응식
[S:1]1[CH:5]=[CH:4][S:3][C:2]1=[C:6]([C:20]([O:22][CH3:23])=[O:21])[C:7]([NH:9][CH:10]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([OH:13])=O)=[O:8].C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:37]([NH:40][CH2:41][CH2:42][CH3:43])[CH2:38][CH3:39]>ClCCl>[CH2:37]([N:40]([CH2:41][CH2:42][CH3:43])[C:11](=[O:13])[CH:10]([NH:9][C:7](=[O:8])[C:6](=[C:2]1[S:1][CH:5]=[CH:4][S:3]1)[C:20]([O:22][CH3:23])=[O:21])[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH2:38][CH3:39]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8902DipropylamineHCID 10928Ethyl chloroformateHCID 154321262-((2-(1,3-Dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-methoxy-5-oxopentanoic acid

생성물 1

HCID 15432127Methyl 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-oxopentanoate수율 57%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

2-((2-(1,3-Dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-methoxy-5-oxopentanoic acid (4) (239 g) was dissolved in dichloromethane (1.5 l), followed by the addition of 70.7 g of triethylamine. To the resulting solution, 71.8 g of ethyl chlorocarbonate were added dropwise at 5-10° C. under stirring over 30 minutes. Subsequent to further stirring at 15-20° C. for 3 hours, di-n-propylamine (70.7 g) was added dropwise at 5-10° C., followed by stirring at room temperature for 12 hours. The solvent was removed under reduced pressure, and ethyl acetate (2 l) was then added to the residue. The resulting precipitate was filtered off. After the ethyl acetate layer was washed with 0.5 N hydrochloric acid and then with water, the solvent was removed under reduced pressure. Diethyl ether (800 ml) was added to the residue and the resulting precipitate was collected by filtration, whereby methyl 5-(dipropylamino)-4-((2-(1,3-dithiol-2-ylidene)-3-methoxy-3-oxopropanoyl)amino)-5-oxopentanoate (5) (113 g, yield: 57%) was obtained as pale yellow crystals.

후처리

  1. stirringSubsequent to further stirring at 15-20° C. for 3 hours
  2. stirringby stirring at room temperature for 12 hours
  3. customThe solvent was removed under reduced pressure, and ethyl acetate (2 l)
  4. additionwas then added to the residue
  5. filtrationThe resulting precipitate was filtered off
  6. washAfter the ethyl acetate layer was washed with 0.5 N hydrochloric acid
  7. customwith water, the solvent was removed under reduced pressure
  8. additionDiethyl ether (800 ml) was added to the residue
  9. filtrationthe resulting precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-ec450706ddcf45e8a78a5d30044bc27d
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962509

반응 노트

불러오는 중…