Ethyl Acetate → HCID 70000534, compound

HRID 1634044Notes

Reaction equation

HRID 1634044 reaction equation
[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([NH2:18])[CH:16]=[CH:17][C:10]=2[N:9]([CH3:19])[C:8](=[O:20])[CH2:7]1)[CH3:2].[CH2:22]([N:29]=[C:30]=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCOC(C)=O>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][N:6]1[C:12](=[O:13])[C:11]2[CH:14]=[C:15]([NH:18][C:30]([NH:29][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:31])[CH:16]=[CH:17][C:10]=2[N:9]([CH3:19])[C:8](=[O:20])[CH2:7]1)[CH3:2]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 76639Benzyl isocyanateHCID 70000117HCID 70000117, compound

Product 1

HCID 70000534HCID 70000534, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of (7-amino-1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetic acid ethyl ester (0.65 g, 2.23 mmol) in DMF (5 ml) was added benzylisocyanate (0.5 g, 3.75 mmol) and DMAP (5 mg). After 2 h at 60° C. the reaction mixture was poured into AcOEt (70 ml), washed with aqueous KHSO4 (0.1 N) and water. After drying over Na2SO4 and evaporation of the solvents the residue was purified by chromatography (dichloromethane/MeOH 19:1) to give [7-(3-benzyl-ureido)-1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetic acid ethyl ester (930 mg, 2.19 mmol): mp. 151° C.; MS (EI): 424 (M)+.

Workup

  1. washwashed with aqueous KHSO4 (0.1 N) and water
  2. dry with materialAfter drying over Na2SO4 and evaporation of the solvents the residue
  3. customwas purified by chromatography (dichloromethane/MeOH 19:1)

Sources & evidence

ORD record
ord-a560bfe44f4f40d189041f6a13c826b6
Source dataset
uspto-grants-2003_01
Patent number
US06506744B1

Reaction notes

Loading…