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

HRID 85406

Reaktionsgleichung

Reaktionsgleichung von HRID 85406
[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]

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-f050b6c21cf142d6a755dc86bdb2d6d3
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846972B2

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