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

HRID 1737939ノート

反応式

HRID 1737939 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ec450706ddcf45e8a78a5d30044bc27d
出典データセット
uspto-grants-1999_10
特許番号
US05962509

反応ノート

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