Benzyl isocyanate → HCID 69999628, compound

HRID 1634045Notes

Reaction equation

HRID 1634045 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][NH:7][C:8](=[O:27])[CH2:9][N:10]1[C:16](=[O:17])[C:15]2[CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=[CH:21][C:14]=2[N:13]([CH3:25])[C:12](=[O:26])[CH2:11]1)[CH3:2].[CH2:29]([N:36]=[C:37]=[O:38])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:28])[CH2:5][CH2:6][NH:7][C:8](=[O:27])[CH2:9][N:10]1[C:16](=[O:17])[C:15]2[CH:18]=[C:19]([NH:22][C:37]([NH:36][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:38])[CH:20]=[CH:21][C:14]=2[N:13]([CH3:25])[C:12](=[O:26])[CH2:11]1)[CH3:2]

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 69999877HCID 69999877, compound

Product 1

HCID 69999628HCID 69999628, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Catalytic hydrogenation of 3-[2-(1-methyl-7-nitro-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl)-acetylamino]-propionic acid ethyl ester in EtOH in the presence of 10% Pd/C at RT and atmospheric pressure followed by acylation with benzylisocyanate as described in Example 1d) gave 3-[2-[7-(3-benzyl-ureido)-1-methyl-2,5-dioxo-1,2,3,5-tetrahydro-benzo[e][1,4]diazepin-4-yl]-acetylamino]-propionic acid ethyl ester: mp. 100-102° C.; MS (ISP): 496 (M+1)+.

Workup

  1. customat RT

Sources & evidence

ORD record
ord-2b21f20f073d4875823ec128a988647a
Source dataset
uspto-grants-2003_01
Patent number
US06506744B1

Reaction notes

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