2,6-Lutidine → S-(2-Aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester

HRID 1462486Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1462486
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].N1C(C)=CC=CC=1C.[CH3:17][C:18]([CH3:30])([O:20][C:21]([NH:23][C:24](=[CH2:29])[C:25]([O:27][CH3:28])=[O:26])=[O:22])[CH3:19]>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][CH2:29][C@@H:24]([C:25]([O:27][CH3:28])=[O:26])[NH:23][C:21]([O:20][C:18]([CH3:30])([CH3:17])[CH3:19])=[O:22]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 87132-AminothiophenolHCID 10932500Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

Produkt 1

HCID 131713585S-(2-Aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 2-amino-thiophenol (1.9 g., 15.4 mmole), methylene chloride (15 ml.), and 2,6-lutidine (1.8 ml., 1.0 eq.) at -20° (chloroform dry ice) is added 2-[[(1,1-dimethylethoxy)carbonyl]amino]-2-propenoic acid, methyl ester (3.0 g., 1.0 eq.) dropwise over 5 minutes. After one hour the cooling bath is removed and the reaction mixture is stirred for an additional 16 hours. The reaction mixture is diluted with ethyl acetate and washed with saturated sodium bicarbonate, water, brine, dried (MgSO4), and evaporated. The residue (4.1 g.) is chromatographed on silica (125 g.) eluting with hexane/ethyl acetate (5:1) to give 2.5 g. of S-(2-aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester as an oil after evaporation.

Aufarbeitung

  1. customAfter one hour the cooling bath is removed
  2. additionThe reaction mixture is diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue (4.1 g.) is chromatographed on silica (125 g.)
  7. washeluting with hexane/ethyl acetate (5:1)
  8. customto give 2.5 g
  9. customof S-(2-aminophenyl)-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine, methyl ester as an oil after evaporation

Quellen und Nachweise

ORD-Eintrag
ord-c225e1d454ab43dea6a130265d55beb6
Quelldatensatz
uspto-grants-1984_07
Patentnummer
US04460579

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