5-(Tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid → 2-Amino-5-({[(tert-butoxy)carbonyl]amino}methyl)benzoic acid

HRID 509479Notes

Reaction equation

HRID 509479 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:19]([O-])=O)=[C:14]([CH:18]=1)[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOCC.[Pd]>[NH2:19][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:18][C:14]=1[C:15]([OH:17])=[O:16]

Participants

5

Reactant 1

HCID 666971495-(Tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid

Product 1

HCID 666971382-Amino-5-({[(tert-butoxy)carbonyl]amino}methyl)benzoic acidYield 49.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-(tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid (21.0 g, 70.9 mmol) in methanol (210 mL) and palladium/carbon (2 g) 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-5-(tert-butoxycarbonylamino-methyl)-benzoic acid as a brown solid (9.3 g, 49% 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-8e04efa2b80b4699a737e042b36d05a1
Source dataset
uspto-grants-2015_08
Patent number
US09096573B2

Reaction notes

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