Ammonium formate → Carbamic acid, [6-[(4-aminobenzoyl)amino]hexyl]-, 1,1-dimethylethyl ester

HRID 732847Notes

Reaction equation

HRID 732847 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15](=[O:25])[C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58720809HCID 58720809, compound

Product 1

HCID 58720810Carbamic acid, [6-[(4-aminobenzoyl)amino]hexyl]-, 1,1-dimethylethyl esterYield 105.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above amide (265 mg, 0.750 mmol) was dissolved in EtOH (25 mL). The reaction mixture was charged with ammonium formate (500 mg) and 10% palladium on carbon (100 mg) and stirred for 4 days at ambient temperature. The reaction was filtered through diatomaceous earth and concentrated to recover 265 mg of [6-(4-amino-benzoylamino)-hexyl]-carbamic acid tert-butyl ester as a white crystalline solid (quantitative yield).

Workup

  1. filtrationThe reaction was filtered through diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ef9040cae8ba4599ac2e204884e49b07
Source dataset
uspto-grants-2009_09
Patent number
US07588899B2

Reaction notes

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