Isatoic Anhydride → (11aR)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione

HRID 1976227Notes

Reaction equation

[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=O.[NH:13]1[CH2:20][CH2:19][CH2:18][C@@H:14]1C(O)=O>>[CH2:19]1[C@@H:20]2[C:5](=[O:12])[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=3[C:2](=[O:4])[N:13]2[CH2:14][CH2:18]1

Participants

Reactant 2

HCID 8359Isatoic Anhydride

HCID 8988D-Proline

Product 1

HCID 677115(11aR)-2,3-Dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dioneYield 78.9%

Procedure

The same procedures used in the method B in Reference Example 19 were repeated except for the use of isatoic anhydride and D-proline to form the title compound. Yield 78.9%.

Sources & evidence

ORD record: ord-bc3439b5ae454d738203c6c8c0964cfb
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225306B1

Reaction notes

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