HCID 22405144, compound → HCID 22405176, compound

HRID 441238Notes

Reaction equation

HRID 441238 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[N+:35]([O-])=O)[C:12]([N:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[N:18]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:17](=[O:31])[CH2:16][CH2:15]1)=[O:13])C1C=CC=CC=1.[H][H]>[Pd].C(O)C.O1CCOCC1>[NH2:35][C:34]1[CH:33]=[CH:32][C:11]([C:12]([N:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:17](=[O:31])[CH2:16][CH2:15]2)=[O:13])=[CH:10][C:9]=1[OH:8]

Participants

6

Reactant 2

HCID 22405144HCID 22405144, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22405176HCID 22405176, compoundYield 89.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-(3-benzyloxy-4-nitrobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (2.2 g), 10% palladium on carbon (220 mg) in ethanol (30 ml) and 1,4-dioxane (15 ml) was stirred under 4 atmospheric pressure of hydrogen at ambient temperature for 7 hours. The reaction mixture was filtered through a bed of celite, concentrated and purified by silica gel column chromatography (SiO2 60 g, ethyl acetate:n-hexane =2:1) to give 5-(4-amino-3-hydroxybenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (1.5 g).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite,
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography (SiO2 60 g, ethyl acetate:n-hexane =2:1)

Sources & evidence

ORD record
ord-4e3f079528334523915f96101dd53467
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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