Ethanol → erythro-N-Boc-L-cyclohexylalanine epoxide

HRID 253560

Reaction equation

HRID 253560 reaction equation
Cl[CH2:2][C@@H:3]([OH:20])[C@@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.CCO>[OH-].[Na+].O>[CH:6]1([CH2:5][C@H:4]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:3]2[CH2:2][O:20]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 702EthanolHCID 10470386HCID 10470386, compound

Product 1

HCID 9816868erythro-N-Boc-L-cyclohexylalanine epoxideYield 95.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

tert-Butyl (2S,3S)-4-chloro-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (1 g, 3.28 mmol) was dissolved in a solution of 0.71 N NaOH in EtOH (5.6 mL, 3.95 mmol, 1.2 eq). After stirring for 1 h, the mixture was concentrated to give a residue, which was dissolved in water and extracted with EtOAc (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give tert-butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (0.84 g, 95%). 1H NMR: 0.83 (m, 1H), 0.95 (m, 1H), 1.10-1.42 (m, 5H), 1.45 (s, 9H), 1.68 (m, 5H), 1.76 (m, 1H), 2.72 (m, 2H), 2.83 (m, 1H), 3.55 (m, 1H), 4.38 (m, 1H). MS (E/Z): 270 (M+H+).

Workup

  1. concentrationthe mixture was concentrated
  2. customto give a residue, which
  3. extractionextracted with EtOAc (3×15 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7b2c713abc5c47bfa6b531769b6005e6
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Linked notes

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