Salicylic Acid → (R)-methyl 2-(2-hydroxybenzamido)-3-mercaptopropanoate

HRID 85406노트

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HRID 85406 반응식
[C:1]([OH:10])(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].Cl.[CH3:12][O:13][C:14](=[O:19])[C@H:15]([CH2:17][SH:18])[NH2:16].CCN=C=NCCCN(C)C.CN1CCOCC1>CC#N.CCOC(C)=O>[OH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([NH:16][C@@H:15]([CH2:17][SH:18])[C:14]([O:13][CH3:12])=[O:19])=[O:10]

참가 물질

7

반응물 4

HCID 338Salicylic AcidHCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2733208L-Cysteine, methyl ester, hydrochloride

생성물 1

HCID 10015224(R)-methyl 2-(2-hydroxybenzamido)-3-mercaptopropanoate

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

Separately, salicylic acid (152 mg, 1.10 mmol) was taken up in CH3CN (10 mL) along with L-cysteine methyl ester hydrochloride (189 mg, 1.10 mmol), EDCI (350 mg) and N-methylmorpholine (120 μL). 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 over Na2SO4 and concentrated under reduced pressure to afford crude (R)-methyl 2-(2-hydroxybenzamido)-3-mercaptopropanoate. This material was then taken up in CH3CN (3 mL) 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 (315 mg, 0.7 mmol) and stirred at room temperature for 30 minutes. The reaction mixture was then concentrated under reduced pressure. Purification by silica gel chromatography (CH2Cl2) afforded (R)-methyl 3-(1-(2-(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenamidoethyl)-2,5-dioxopyrrolidin-3-ylthio)-2-(2-hydroxybenzamido)propanoate (140 mg). Mass calculated for C39H51N3O7S: 705.34; found: [M+H]+=706.

후처리

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

출처 및 근거

ORD 기록
ord-f050b6c21cf142d6a755dc86bdb2d6d3
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846972B2

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