4-Methylmorpholine → methyl(2S)-3,3-dimethyl-2-{[(4-nitrophenoxy)carbonyl]amino}butanoate

HRID 1174221Notes

Reaction equation

HRID 1174221 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:11])[C@H:5]([C:7]([CH3:10])([CH3:9])[CH3:8])[NH2:6].Cl[C:13]([O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:14].CN1CCOCC1>ClCCl>[CH3:8][C:7]([CH3:10])([CH3:9])[C@H:5]([NH:6][C:13]([O:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[O:14])[C:4]([O:3][CH3:2])=[O:11]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 16217630Methyl L-tert-leucinate hydrochloride

Product 1

HCID 58412867methyl(2S)-3,3-dimethyl-2-{[(4-nitrophenoxy)carbonyl]amino}butanoateYield 109.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of L-tert-leucine methyl ester hydrochloride (0.300 g, 1.65 mmol) in dichloromethane (4 mL) at 0° C. was treated with 4-nitrophenyl chloroformate (0.366, 1.82 mmol) and N-methyl morpholine (0.380 mL, 3.46 mmol), and the mixture was stirred at 25° C. for 64 hours. The reaction was partitioned between dichloromethane and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated to give the title compound (0.562 g, quantitative), which was used without further purification.

Workup

  1. customThe reaction was partitioned between dichloromethane and saturated NaHCO3
  2. washthe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bf9cab44943d42aa8a099db44a285d91
Source dataset
uspto-grants-2010_11
Patent number
US07834043B2

Reaction notes

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