Dimethylformamide dimethyl acetal → 3(R,S)-[(Benzyloxycarbonyl)amino]-5-cydohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

HRID 1490099Notes

Reaction equation

HRID 1490099 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[NH:14][C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30]OC(OC)N(C)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=2[N:14]([CH3:30])[C:13]1=[O:29])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal2×HCID 135413400Z-(R,S)-3-amino-5-cyclohexyl-2-oxo-1,4-benzodiazepine

Product 1

HCID 152352853(R,S)-[(Benzyloxycarbonyl)amino]-5-cydohexyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a refluxing solution of 3(R,S)-[(benzyloxycarbonyl)amino]-5-cyclohexyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (5 g) in anhydrous toluene (400 ml) was added dimethylformamide dimethylacetal (7.3 ml) and the mixture was refluxed for 3.5 hours under nitrogen before additional dimethylformamide dimethyl acetal (1 ml) was added. After a further 50 minutes at reflux, solvents were removed under vacuum and the residue was triturated with diethyl ether (50 ml). The white solid was collected by filtration, washed with diethyl ether (2×20 ml) and dried to give the title compound (5 g); mp 205°-207° C.; dH (360 MHz, CDCl3) 7.55-7.25 (9H, m), 6.52 (1H, d, J=8.0 Hz), 5.10 (3H, m), 3.36 (3H, s), 2.76 (1H, m), 2.04-1.03 (10H, m).

Workup

  1. additionwas added
  2. temperatureAfter a further 50 minutes at reflux
  3. customsolvents were removed under vacuum
  4. customthe residue was triturated with diethyl ether (50 ml)
  5. filtrationThe white solid was collected by filtration
  6. washwashed with diethyl ether (2×20 ml)
  7. customdried

Sources & evidence

ORD record
ord-629eed401e8f4fd8a37c63bee4333c30
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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