Ethanol → HCID 66782705, compound

HRID 1096184Notes

Reaction equation

HRID 1096184 reaction equation
[H-].[Na+].C(O[C:6](=O)[CH2:7][C@@H:8]([N:10]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:11][C:12]([O:14]CC)=O)C)C.[CH3:25]CO>C1(C)C=CC=CC=1.CCOC(C)=O.Cl>[CH2:17]([N:10]1[CH2:8][C@@H:7]([CH3:6])[CH2:25][C:12](=[O:14])[CH2:11]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 11748816HCID 11748816, compound

Product 1

HCID 66782705HCID 66782705, compoundYield 43%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a suspension of NaH (55% dispersion in mineral oil, 6.4 g, 14 mmol) in toluene (90 ml) was added (S)-3-(benzyl-ethoxycarbonylmethyl-amino)-butyric acid ethyl ester (20.3 g, 0.06 mol) in toluene (10 ml), followed by EtOH (1 ml). A vigorous reaction ensued, after 15 minutes the reaction was diluted with EtOAc, washed with 10% aq. citric acid solution, dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography (EtOAc/heptane 1:9) affording a complex mixture of diastereomers (7.2 g, 42%). A portion of this material (3.5 g, 13 mmol) was dissolved in 25% aq. HCl solution (20 ml) and heated in a loosely closed tube at 120° C. for 36 h. The solvent was evaporated, the residue redissolved in CH2Cl2, washed with sat. aq. NaHCO3 solution, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc/heptane 1:4) afforded the titled product as a crystalline solid (1.1 g, 43%). MS (ISP)=204.3 (M+H)+.

Workup

  1. customA vigorous reaction ensued
  2. washwashed with 10% aq. citric acid solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography (EtOAc/heptane 1:9)
  6. customaffording
  7. additiona complex mixture of diastereomers (7.2 g, 42%)
  8. customThe solvent was evaporated
  9. dissolutionthe residue redissolved in CH2Cl2
  10. washwashed with sat. aq. NaHCO3 solution
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customPurification by flash column chromatography (EtOAc/heptane 1:4)

Sources & evidence

ORD record
ord-8fa0b3fadd5549c8be0b30c3cce6006a
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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