HCID 66642923, compound → HCID 66643161, compound

HRID 1868254Notes

Reaction equation

HRID 1868254 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:11]=1[C:12]([OH:14])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOCC.[Pd]>[NH2:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:11]=1[C:12]([OH:14])=[O:13]

Participants

5

Reactant 1

HCID 66642923HCID 66642923, compound

Product 1

HCID 66643161HCID 66643161, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino-methyl)-6-nitro-benzoic acid (2.19 g, 75 mmol) in methanol (530 mL) and palladium/carbon (0.2 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 foamy brown oil, which was stirred in ether (300 mL) overnight. The suspension was filtered to give 2-amino-6-(tert-butoxycarbonylamino-methyl)-benzoic acid as a yellow solid (13.0 g, 65% 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 foamy brown oil, which
  5. filtrationThe suspension was filtered

Sources & evidence

ORD record
ord-99ea7177c7724eba8cb4199d904fcf8b
Source dataset
uspto-grants-2009_12
Patent number
US07635700B2

Reaction notes

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