L-Proline → (S)-1,2,3,11a-tetrahydro-6-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

HRID 67423

Reaktionsgleichung

Reaktionsgleichung von HRID 67423
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[NH:12][C:11](=[O:13])[O:10][C:8](=O)[C:7]=12.[NH:14]1[CH2:21][CH2:20][CH2:19][C@H:15]1C(O)=O>CS(C)=O>[CH3:1][C:2]1[C:7]2[C:8](=[O:10])[N:14]3[CH2:21][CH2:20][CH2:19][C@H:15]3[C:11](=[O:13])[NH:12][C:6]=2[CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 145742L-ProlineHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

Produkt 1

HCID 13891432(S)-1,2,3,11a-tetrahydro-6-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A solution of 13.6 g (0.0768 mol) of 6-methylisatoic acid anhydride and 8.8 g (0.0768 mol) of L-proline is heated at 110° C. for 1 hour in 75 ml of dimethyl sulphoxide. Subsequently, the mixture is evaporated to dryness in a high vacuum and the residue is recrystallised from ethyl acetate with the addition of active carbon. There is obtained (S)-1,2,3,11a-tetrahydro-6-methyl-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H)-dione of melting point 212°-214° C.

Aufarbeitung

  1. customSubsequently, the mixture is evaporated to dryness in a high vacuum
  2. customthe residue is recrystallised from ethyl acetate with the addition of active carbon

Quellen und Nachweise

ORD-Eintrag
ord-3c83a733826840d689109ed1ab7abf7e
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346032

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