HCID 68731586, compound → HCID 68732363, compound

HRID 509511Notes

Reaction equation

HRID 509511 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[C:12]([N+:19]([O-])=O)[CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOCC.[Pd]>[NH2:19][C:12]1[CH:11]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:18]=[CH:17][C:13]=1[C:14]([OH:16])=[O:15]

Participants

5

Reactant 1

HCID 68731586HCID 68731586, compound

Product 1

HCID 68732363HCID 68732363, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-(tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid (56.57, 190.9 mmol) in methanol (250 mL) and palladium/carbon (5.66 g, 10% weight) was hydrogenated with a Parr-shaker overnight at 51 psi. The black mixture was filtered through a pad of Celite, and the filtrate was evaporated to give a brown oil, which was stirred in ether (300 mL) overnight. The ether slurry was filtered to give 2-amino-4-(tert-butoxycarbonylamino-methyl)-benzoic acid as a brown solid (42.0 g, 84% yield). The product was used in the next step without further purification.

Workup

  1. customwas hydrogenated with a Parr-shaker overnight at 51 psi
  2. filtrationThe black mixture was filtered through a pad of Celite
  3. customthe filtrate was evaporated
  4. customto give a brown oil, which
  5. filtrationThe ether slurry was filtered

Sources & evidence

ORD record
ord-48fe4c0c320b4262a0dcc177e8636036
Source dataset
uspto-grants-2015_08
Patent number
US09096573B2

Reaction notes

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