4-Methylmorpholine → (R,E)-methyl 4-(3-mercapto-1-methoxy-1-oxopropan-2-ylamino)-4-oxobut-2-enoate

HRID 869788

反応式

HRID 869788 の反応式
[C:1]([O:8][CH3:9])(=[O:7])/[CH:2]=[CH:3]/[C:4]([O-:6])=O.Cl.[CH3:11][O:12][C:13](=[O:18])[C@H:14]([CH2:16][SH:17])[NH2:15].CCN=C=NCCCN(C)C.CN1CCOCC1>CC#N.CCOC(C)=O>[SH:17][CH2:16][C@H:14]([NH:15][C:4](=[O:6])/[CH:3]=[CH:2]/[C:1]([O:8][CH3:9])=[O:7])[C:13]([O:12][CH3:11])=[O:18]

参加物

7

反応物 4

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2733208L-Cysteine, methyl ester, hydrochlorideHCID 21721168(E)-4-methoxy-4-oxobut-2-enoate

生成物 1

HCID 86655430(R,E)-methyl 4-(3-mercapto-1-methoxy-1-oxopropan-2-ylamino)-4-oxobut-2-enoate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Separately, mono methyl fumarate (100 mg, 0.77 mmol) was taken up in 4 mL of CH3CN along with L-cysteine methyl ester hydrochloride (132 mg, 0.77 mmol), EDCI (245 mg, 0.77 mmol) and N-methylmorpholine (85 μL, 0.77 mmol). The reaction mixture was stirred at room temperature for 3 h. It was then diluted with EtOAc. The organic layer was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried (Na2SO4) and concentrated under reduced pressure to afford crude (R,E)-methyl 4-(3-mercapto-1-methoxy-1-oxopropan-2-ylamino)-4-oxobut-2-enoate. This material was then taken up in 3 mL of CH3CN along with (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2,5-dioxo-2H-pyrrol-1(5H)-yl)ethyl)docosa-4,7,10,13,16,19-hexaenamide (173 mg, 0.38 mmol) and stirred at room temperature for 30 min. The reaction mixture was then concentrated under reduced pressure. Purification by chromatography (CH2Cl2) afforded 60 mg of (E)-methyl 4-((R)-3-(1-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2,5-dioxopyrrolidin-3-ylthio)-1-methoxy-1-oxopropan-2-ylamino)-4-oxobut-2-enoate (22%). MS (EI) calcd for C37H51N3O8S: 697.34. found: 698 (M+1).

後処理

  1. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4291ff60cc144a75a5d71713ee327fd4
出典データセット
uspto-grants-2015_03
特許番号
US08969354B2

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