Methyl chloroformate → HCID 11746656, compound

HRID 923410Notes

Reaction equation

HRID 923410 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].C([O-])([O-])=O.[Na+].[Na+].Cl[C:21]([O:23][CH3:24])=[O:22]>C1COCC1>[CH3:24][O:23][C:21]([NH:1][C@@H:2]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4])=[O:22]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 2724505(S)-2-amino-4-phenylbutanoic acid

Product 1

HCID 11746656HCID 11746656, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-amino-4-phenylbutanoic acid (0.50 g, 2.8 mmol) was suspended in 1M Na2CO3 (8.4 mL, 8.4 mmol) and then a solution of methyl chloroformate (0.32 mL, 4.2 mmol) in THF (4.0 mL) was added and the mixture was stirred vigorously at room temperature for 4 hours. The mixture was then concentrated under reduced pressure and the residue was dissolved in water and made acidic with 0.1N HCl. The mixture was extracted with ethyl acetate, dried over Na2SO4, filtered and concentrated under reduced pressure to provide the title compound (0.64 g, 97% yield).

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa09a23b948f47dcbd942c9259503d99
Source dataset
uspto-grants-2016_03
Patent number
US09278922B2

Reaction notes

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