Ethyl Acetate → HCID 25106944, compound

HRID 2265262Notes

Reaction equation

HRID 2265262 reaction equation
[N:1]([C@@H:4]([CH:8]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:5]([OH:7])=[O:6])=[N+]=[N-].CCOC(C)=O>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CO>[NH2:1][C@@H:4]([CH:8]([C:9]1[CH:10]=[CH:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:16]1[CH:17]=[CH:18][C:19]([Cl:22])=[CH:20][CH:21]=1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 86726383HCID 86726383, compound

Product 1

HCID 25106944HCID 25106944, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 887MethanolSolvent

Procedure

(S)-2-Azido-3,3-bis-(4-chloro-phenyl)-propionic acid (0.98 g, 2.9 mmol), Lindlar's catalyst (307 mg, 5 mol % Pd), and EtOAc (29 mL) was placed in a 500 mL Parr bottle. The bottle was pressurized with 50 psi of H2 and shaken overnight in a Parr shaker apparatus. The mixture was diluted with MeOH, and the catalyst was removed by filtration through diatomaceous earth, rinsing with MeOH. The filtrate was concentrated to provide 0.90 g (100%) of the desired amino acid as a white solid. MS (ESI−): mass calcd. for C15H13Cl2NO2, 309; m/z found, 308 [M−H]−. 1H NMR (400 MHz, CD3OD): 7.41-7.22 (m, 8H), 4.46 (d, J=9.1, 1H), 4.26 (d, J=9.1, 1H).

Workup

  1. customthe catalyst was removed by filtration through diatomaceous earth
  2. washrinsing with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-c7a5deeb32bf401d8c6e231a7bc2e015
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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