Acetonitrile → cis-N-Carbobenzyloxy-4-[[(methylamino)carbonyl]oxy]-L-proline, methyl ester

HRID 1856002

Reaktionsgleichung

Reaktionsgleichung von HRID 1856002
[C:1]([N:11]1[CH2:19][C@@H:18]([OH:20])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(#N)C.[CH3:24][N:25]=[C:26]=[O:27]>C(N(CC)CC)C>[C:1]([N:11]1[CH2:19][C@@H:18]([O:20][C:26]([NH:25][CH3:24])=[O:27])[CH2:17][C@H:12]1[C:13]([O:15][CH3:16])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 12228Methyl IsocyanateHCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

Produkt 1

HCID 131711848cis-N-Carbobenzyloxy-4-[[(methylamino)carbonyl]oxy]-L-proline, methyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a stirred solution of 5.4 g. (0.019 mole) of N-carbobenzyloxy-cis-4-hydroxy-L-proline, methyl ester, in 120 ml. of acetonitrile is added 5.4 ml. of triethylamine, followed by 5.4 ml. of methyl isocyanate. After keeping overnight at room temperature and refluxing for two hours, the reaction mixture is worked up as in Example 1c to give 5.6 g (86%) of a pale yellow viscous oil.

Aufarbeitung

  1. temperaturerefluxing for two hours

Quellen und Nachweise

ORD-Eintrag
ord-2fdfd0183bb64ac9a910b5f1b10c4985
Quelldatensatz
uspto-grants-1980_08
Patentnummer
US04217359

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