HCID 66935020, compound → HCID 67462864, compound

HRID 554821Notes

Reaction equation

HRID 554821 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C@@H:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:17]=1[O:23][CH3:24])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 66935020HCID 66935020, compound

Product 1

HCID 67462864HCID 67462864, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl (2R)-3-[(tert-butoxycarbonyl)amino]-2-(5-chloro-2-methoxybenzyl)propanoate (1.0 g, 98%ee) in acetonitrile (10 ml), 1,8-diazabicyclo[5.4.0]undecene-7 (510.5 mg) was added and the mixture was stirred under heating and refluxed for 5 hours. After the solvent was distilled off in vacuo, ethyl acetate was added to the obtained residue, and the organic layer was washed with 1N hydrochloric acid, and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel column chromatography to obtain the title compound (913 mg, 0%ee) as an oily substance. The 1H-NMR spectral data matches with those of Example 316.

Workup

  1. temperatureunder heating
  2. temperaturerefluxed for 5 hours
  3. distillationAfter the solvent was distilled off in vacuo, ethyl acetate
  4. additionwas added to the obtained residue
  5. washthe organic layer was washed with 1N hydrochloric acid
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off in vacuo
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f070fad18c3451e9a09d5f0f87dfd3c
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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