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

HRID 743698Notes

Reaction equation

HRID 743698 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[N:18]=[C:17]([CH:19]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[NH:14][C:13]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31]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[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[C:16]2[CH:26]=[CH:27][CH:28]=[CH:29][C:15]=2[N:14]([CH3:31])[C:13]1=[O:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1358436063(R,S)-[(Benzyloxycarbonyl)amino]-5-cycloheptyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 214804783(R,S)-[(Benzyloxycarbonyl)amino]-5-cycloheptyl-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

3(R,S)-[(Benzyloxycarbonyl)amino]-5-cycloheptyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one (Example 1, Step 3, 500 mg) in anhydrous toluene (40 ml) was heated to reflux. A solution of dimethylformamide dimethyl acetal (786 μl) in anhydrous toluene (10 ml) was added dropwise and the mixture was heated at reflux for a further hour. The solvent was evaporated and the residue triturated with diethyl ether to afford the title compound (441 mg) as a colourless solid. 1H NMR (360 MHz, CDCl3) δ 1.24-1.90 (11H, m), 2.00-2.14 (1H, m), 2.90-3.00 (1H, m), 3.40 (3H, s), 5.04-5.18 (3H, m), 6.52 (1H, d, J=7.5 Hz), 7.24-7.60 (9H, m). TLC (silica, petrol (60/80): ethyl acetate 2:1). Rf=0.30.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for a further hour
  3. customThe solvent was evaporated
  4. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-7f602d1022ac41bc9a7c8a92e7230d14
Source dataset
uspto-grants-1996_09
Patent number
US05556969

Reaction notes

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