Isatoic Anhydride → (3S)-3-Methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dione

HRID 1633506Notes

Reaction equation

HRID 1633506 reaction equation
[NH2:1][C@@H:2]([C:4]([OH:6])=O)[CH3:3].[C:7]12[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[NH:12]C(=O)O[C:8]2=[O:9]>N1C=CC=CC=1>[CH3:3][C@H:2]1[NH:1][C:8](=[O:9])[C:7]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH:12][C:4]1=[O:6]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 71080D-Alanine

Product 1

HCID 12282507(3S)-3-Methyl-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2,5-dioneYield 20.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure of Example 5, D-alanine (73.6 mmol) and isatoic anhydride (61.3 mmol) were allowed to reflux in pyridine (50 mL) to give (3R)-3-methyl-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (12.7 mmol) as a light brown solid.

Sources & evidence

ORD record
ord-a26ac89d636d4042a856f006ad0e83e6
Source dataset
uspto-grants-2003_01
Patent number
US06503900B2

Reaction notes

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