Water → HCID 90051744, compound

HRID 2284703Notes

Reaction equation

HRID 2284703 reaction equation
[C:1]([N:8]([CH3:14])[C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:27]=[CH:28][CH:29]=1)[NH2:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.C(OCC)(=O)C>O1CCCC1.ClC(OCC(C)C)=O.CN1CCOCC1>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([NH:26][C:11](=[O:13])[C@@H:9]([N:8]([CH3:14])[C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH3:10])[CH:27]=[CH:28][CH:29]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 928923-BenzyloxyanilineHCID 7009590(2S)-2-(((tert-butoxy)carbonyl)(methyl)amino)propanoic acid

Product 1

HCID 90051744HCID 90051744, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolventHCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of N-Boc-N-methyl-L-alanine (561 mg) in tetrahydrofuran (14 mL), isobutyl chloroformate (362 μL) and N-methylmorpholine (303 μL) were added under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture, 3-benzyloxyaniline (500 mg) was added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture, water and ethyl acetate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate) to obtain (S)-tert-butyl (1-((3-(benzyloxy)phenyl)amino)-1-oxopropan-2-yl)(methyl)carbamate (E15, 903 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 70% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-7d45d6273f234fb1a891c73b329b3c81
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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