Acetic Anhydride → HCID 86758535, compound

HRID 989638Notes

Reaction equation

HRID 989638 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[NH:13][CH:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:11](=[O:19])[N:10]([CH3:20])[CH2:9][C:8]=2[CH:21]=1)([OH:3])=[O:2].[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(O)(=O)C>[C:22]([N:13]1[C:7]2[CH:6]=[CH:5][C:4]([C:1]([OH:3])=[O:2])=[CH:21][C:8]=2[CH2:9][N:10]([CH3:20])[C:11](=[O:19])[CH:12]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:24])[CH3:23]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 23505570Methyl 7-carboxy-2,3,4,5-tetrahydro-4-methyl-3-oxo-1h-1,4-benzodiazepine-2-acetate

Product 1

HCID 86758535HCID 86758535, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Methyl (±)-7-carboxy-4-methyl-3-oxo-2,3,4,5-tetrahydro-1H-1,4-benzodiazepine-2-acetate (2.0 g, 8.6 mmol), acetic anhydride (25 mL) and acetic acid (1 mL) were heated to reflux. After 48 h, the reaction was concentrated, and the residue was diluted with H2O (20 mL) and MeOH (15 mL). The resulting solution was concentrated to give the tide compound (1.8 g, 78%): 1H NMR (400 MHz, DMSO-d6) δ1.7-1.8 (s, 3H), 2.2-2.6 (m, 2H), 2.9-3.0 (s, 3H), 3.5-3.6 (s, 3H), 4.2-4.3 (d, 1H), 4.7-4.8 (d, 1H), 5.8-5.9 (t, 1H), 7.5-7.6 (d, 1H), 7.9-8.0 (dd, 1H), 8.1-8.2 (d, 1H); MS (ES) m/e 335.0 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated
  2. additionthe residue was diluted with H2O (20 mL) and MeOH (15 mL)
  3. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-421df1a9e3df4e5f86ec15020b8a258b
Source dataset
uspto-grants-2002_10
Patent number
US06458784B1

Reaction notes

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