HCID 71245349, compound → HCID 73553823, compound

HRID 1186022Notes

Reaction equation

HRID 1186022 reaction equation
C([O:8][C:9](=[O:25])[CH:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:11]([O:13][C:14](=[O:16])[CH3:15])[CH3:12])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:14]([O:13][C@H:11]([CH3:12])[C@H:10]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:9]([OH:25])=[O:8])(=[O:16])[CH3:15]

Participants

4

Reactant 1

HCID 71245349HCID 71245349, compound

Product 1

HCID 73553823HCID 73553823, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl-3-acetoxy-2-(tert-butoxycarbonylamino) butanoate 11 (1.4 g, 3.98 mmol) was dissolved in EtOAc (40 mL), 10% Pd/C (600 mg) was added and reaction mixture was stirred under hydrogen atmosphere for 16 h. The reaction mixture was filtered over celite, solvent was evaporated in vacuo and the crude residue was triturated with hexane to yield (2S,3R)-3-acetoxy-2-(tert-butoxycarbonylamino) butanoic acid 12 (0.7 g, 70%).

Workup

  1. customreaction mixture
  2. filtrationThe reaction mixture was filtered over celite, solvent
  3. customwas evaporated in vacuo
  4. customthe crude residue was triturated with hexane

Sources & evidence

ORD record
ord-296b406175414ed4bab13ea8912a8fa1
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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