Water → HCID 59238187, compound

HRID 2068572Notes

Reaction equation

HRID 2068572 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[C:17]([C:24]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:25])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[C:17]([C:24]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:25])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 962WaterHCID 59238198HCID 59238198, compound

Product 1

HCID 59238187HCID 59238187, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[3-(Methoxycarbonylmethyl-aminocarbonyl)-4-nitro-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester (38.4 g) was dissolved in methanol and 4 g of 10% (wt/wt) palladium on carbon catalyst was added with water (1000 mL) under a nitrogen atmosphere. The mixture was then degassed before stirring under 1 atmosphere of hydrogen gas at room temperature for approximately 8 hours. At this time, the reaction mixture was filtered through celite and washed with copious volumes of methanol. The filtrate was concentrated in vacuo, To the residue was added acetonitrile before evaporation of the solvent. To give 4-[4-amino-3-(methoxycarbonylmethyl-aminocarbonyl)-phenyl]-[1,4]diazepane-1-carboxylic acid tert-butyl ester as a dark green oil: 34.05 g (95%).

Workup

  1. customThe mixture was then degassed
  2. filtrationAt this time, the reaction mixture was filtered through celite
  3. washwashed with copious volumes of methanol
  4. concentrationThe filtrate was concentrated in vacuo, To the residue
  5. additionwas added acetonitrile
  6. custombefore evaporation of the solvent

Sources & evidence

ORD record
ord-c771b36701b3454b8797a567649be294
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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