HCID 86761239, compound → HCID 68769642, compound

HRID 2265240Notes

Reaction equation

HRID 2265240 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([N:15]=[N+]=[N-])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:6]>CCOC(C)=O.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([NH2:15])[C@@H:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=1)[CH3:6]

Participants

4

Reactant 1

HCID 86761239HCID 86761239, compound

Product 1

HCID 68769642HCID 68769642, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,3R)-2-azido-3-(3,4-dichloro-phenyl)-butyric acid methyl ester (0.42 g, 1.46 mmol) in EtOAc (30 mL) was added Lindlar's catalyst. The mixture was hydrogenated at 50 psi. After 16 h, the reaction mixture was filtered through SiO2 and concentrated to afford 0.28 g (74%) of the desired product. 1H NMR (500 MHz, CDCl3): 7.39 (d, J=8.3, 1H), 7.35 (d, J=2.1, 1H), 7.10 (dd, J=8.3, 2.1, 1H), 3.96 (d, J=6.4, 1H), 3.71 (s, 3H), 3.31-3.27 (m, 1H), 1.33 (d, J=7.0, 3H).

Workup

  1. filtrationthe reaction mixture was filtered through SiO2
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-7e8cfda0283c44e38f3268e43b1512ca
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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