HCID 68639140, compound → HCID 68628824, compound

HRID 1253887Notes

Reaction equation

HRID 1253887 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:20][C:21]([OH:23])=[O:22])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[N+:17]([O-])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[NH2:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:20][C:21]([OH:23])=[O:22]

Participants

4

Reactant 1

HCID 68639140HCID 68639140, compound

Product 1

HCID 68628824HCID 68628824, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [tert-butoxycarbonyl-(4-fluoro-2-nitro-benzyl)-amino]-acetic acid (5.11 g, 15.50 mmol) in absolute EtOH (30 mL), was added 10% Pd/C (1.02 g, 20% w/w). The reaction was stirred at r.t. for 5 h under hydrogen atmosphere. After completion of the reaction, as confirmed by TLC, the reaction mixture was filtered through celite bed and was washed with EtOAc (10 mL) and MeOH (10 mL). The solvents were removed in vacuo to afford 2-((2-amino-4-fluorobenzyl) (tert-butoxycarbonyl)amino) acetic acid (4.64 g, 99.9%), which was used as such far the next step without any further purification.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered through celite bed
  3. washwas washed with EtOAc (10 mL) and MeOH (10 mL)
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ee6af96a65ac4d51b26bee464739d596
Source dataset
uspto-grants-2013_06
Patent number
US08455479B2

Reaction notes

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