Benzyl chloroformate → HCID 67263771, compound

HRID 1687941Notes

Reaction equation

HRID 1687941 reaction equation
C([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([O:22][CH3:23])[C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:12]=2[NH:11][C:10](=[O:24])[CH2:9]1)C1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27]>ClCCCl>[CH2:29]([O:28][C:26]([N:8]1[CH2:14][C:13]2[CH:15]=[C:16]([O:22][CH3:23])[C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:12]=2[NH:11][C:10](=[O:24])[CH2:9]1)=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 57853849HCID 57853849, compound

Product 1

HCID 67263771HCID 67263771, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (4-benzyl-7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (900 mg, 3.0 mmol) in 1,2-dichloroethane (150 mL) was added benzyl chloroformate (900 mg, 3.0 mmol). The mixture was warmed to reflux for four hours whereupon LCMS indicated completion of reaction. The mixture was cooled to ambient temperature, washed with brine, dried over magnesium sulfate, filtered and concentrated. Flash chromatography over silica gel (EtOAc-hexanes) gave 7-methoxy-8-nitro-2-oxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepine-4-carboxylic acid benzyl ester (390 mg, 40%) as a yellow solid; 1H NMR (400 MHz, DMSO-d6) δ 10.19 (s, 1H), 7.67 (s, 1H), 7.30 (m, 6H), 5.09 (s, 2H), 4.67 (s, 2H), 3.90 (s, 2H), 3.77 (s, 3H); MS (m/e) 372 (M+1); mp 191° C.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for four hours whereupon LCMS
  3. customcompletion of reaction
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2679d40465c04862bb59a0a21410e010
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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