Water → (S)-2-((S)-1-azido-2-phenylethyl)oxirane

HRID 226215Notes

Reaction equation

HRID 226215 reaction equation
[N:1]([CH:4]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:5]([OH:20])[CH2:6]OS(C1C=CC([N+]([O-])=O)=CC=1)(=O)=O)=[N+:2]=[N-:3].C(OCC)(=O)C.[OH-].[K+].O>C(O)C.C(Cl)Cl>[N:1]([C@H:4]([C@H:5]1[CH2:6][O:20]1)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 866164634-Nitro-benzenesulfonic acid 3-azido-2-hydroxy-4-phenyl-butyl ester

Product 1

HCID 10954320(S)-2-((S)-1-azido-2-phenylethyl)oxiraneYield 95.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g (2.5 mmol) of 4-Nitro-benzenesulfonic acid 3-azido-2-hydroxy-4-phenyl-butyl ester (Kick, E. K.; Ellman, J. A. J. Med. Chem. 1995, 38, 1427-30) in 12 mL of Ethanol and 8 mL of ethyl acetate is treated with KOH (157 mg, 2.8 mmol). After 2 h at rt 10 mL of water is added and 20 mL of CH2Cl2 is added. The organic layer is separated, washed with brine and Na2SO4, and concentrated. Chromatography eluting with hexanes/ethyl acetate 5:1 provides 450 mg (95%) of the desired product. 1H NMR (δ) 7.21-7.36 (m, 5H), 3.58 (dt, 2H, J=9, 5 Hz), 3.05 (m, 1H) 2.97 (dd, 1H, J=13.9, 4.8), 2.77-2.83 (m, 3H).

Workup

  1. customThe organic layer is separated
  2. washwashed with brine and Na2SO4
  3. concentrationconcentrated
  4. washChromatography eluting with hexanes/ethyl acetate 5:1

Sources & evidence

ORD record
ord-c09807d698b64033ad747bd812e792fa
Source dataset
uspto-grants-2009_07
Patent number
US07557137B2

Reaction notes

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