Water → 4-Methanesulfonyl-2-methoxycarbonylamino-butyric acid

HRID 79893Notes

Reaction equation

HRID 79893 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][CH:7]([CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:8]([OH:10])=[O:9].[OH-].[Na+].O>C1COCC1>[CH3:16][S:13]([CH2:12][CH2:11][CH:7]([NH:6][C:2]([O:4][CH3:5])=[O:3])[C:8]([OH:10])=[O:9])(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformate2×HCID 14798Sodium Hydroxide2×HCID 69961Butanoic acid, 2-amino-4-(methylsulfonyl)-

Product 1

HCID 431859814-Methanesulfonyl-2-methoxycarbonylamino-butyric acidYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl chloroformate (2.6 mL, 33 mmol) was added dropwise to a stirred suspension of 2-Amino-4-methanesulfonyl-butyric acid (5.03 g, 27.8 mmol) and NaOH (5 N in H2O, 13.3 mL, 66.6 mmol) in THF (50 mL). After stirring at room temperature for 9 h, additional methyl chloroformate (5.2 mL, 66.6 mmol) and NaOH (5 N in H2O, 30 mL, 150 mmol) were added. After another 14 h, the reaction mixture was poured into H2O. The aqueous phase was washed with DCM 2× then acidified to pH 1 with 10% HCl. The acidified aqueous phase was extracted 3× with EtOAc. The combined organics were dried over MgSO4, filtered and concentrated to provide 4-Methanesulfonyl-2-methoxycarbonylamino-butyric acid (970 mg, 15%).

Workup

  1. waitAfter another 14 h
  2. washThe aqueous phase was washed with DCM 2×
  3. extractionThe acidified aqueous phase was extracted 3× with EtOAc
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ed728ced43b4f5aadad21b51d9c7662
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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