Sodium hydride → Methyl (2-oxo-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-1-yl)acetate

HRID 347643Notes

Reaction equation

[NH:1]1[C:7](=[O:8])[CH2:6][CH2:5][NH:4][C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]1=2.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C>[O:8]=[C:7]1[N:1]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:2]2[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=2[NH:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of 1,3,4,5-tetrahydro-benzo[b][1,4]diazepin-2-one (5.0 g, 30.8 mmol) in DMF (30 ml), at −10° C., was added sodium hydride (1.35 g, 60% dispersion, 33.9 mmol). The mixture was stirred at −10° C. for 15 min, then methyl bromoacetate (2.92 ml, 30.8 mmol) was added. The mixture was stirred at −10° C. for a further 1 h and then concentrated in vacuo. The residue was taken up in EtOAc and washed with brine (3 times), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography on silica (eluant EtOAc) to give a white solid; yield 7.08 g (98%).

Workup

stirringThe mixture was stirred at −10° C. for a further 1 h
concentrationconcentrated in vacuo
washwashed with brine (3 times)
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography on silica (eluant EtOAc)
customto give a white solid

Sources & evidence

ORD record: ord-4f73e2ecaf4d417583ba4cafbb6de363
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07176195B2

Reaction notes

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