Methyl chloroformate → 2-Methoxycarbonylamino-2-phenyl-propionic acid

HRID 1751445Notes

Reaction equation

HRID 1751445 reaction equation
[NH2:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17]>C1COCC1.Cl>[CH3:19][O:18][C:16]([NH:1][C:2]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:6])[C:3]([OH:5])=[O:4])=[O:17]

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 14798Sodium HydroxideHCID 317222-Amino-2-phenylpropanoic acid

Product 1

HCID 624897412-Methoxycarbonylamino-2-phenyl-propionic acidYield 49%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-Amino-2-phenyl-propionic acid (1.00 g, 6.06 mmol) in THF (17 mL), was added aqueous NaOH (6 M, 2.5 mL, 15.0 mmol) and Methyl Chloroformate (0.55 mL, 7.10 mmol). The solution was stirred for 18 h. Aqueous HCl (12 M, 1.5 mL, 18 mmol) was slowly added. The solution was diluted with HCl (1M) and extracted with Et2O (3 times). The combined organic layers were extracted with NaOH (2N, 3 times). The aqueous layers were acidified with HCl (12 N) and extracted with Et2O (3 times). The combined organic layers were dried over MgSO4 and concentrated. The crude oil was diluted in CH2Cl2 and concentrated again to provide 2-Methoxycarbonylamino-2-phenyl-propionic acid (0.66 g, 49%). LCMS-ESI+: calc'd for C11H13NO4: 223.08 (M+); Found: 223.97 (M+H+).

Workup

  1. extractionextracted with Et2O (3 times)
  2. extractionThe combined organic layers were extracted with NaOH (2N, 3 times)
  3. extractionextracted with Et2O (3 times)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated
  6. additionThe crude oil was diluted in CH2Cl2
  7. concentrationconcentrated again

Sources & evidence

ORD record
ord-8731567950b94aff9c48bb0d256b66d5
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

Loading…