Sodium Carbonate → (2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acid

HRID 929933Notes

Reaction equation

HRID 929933 reaction equation
[NH2:1][C@@H:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[C:14](Cl)(=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH2:16]([O:15][C:14]([NH:1][C@@H:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4])=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 80283(-)-2-Aminobutyric acid

Product 1

HCID 7349998(2S)-2-(((Phenylmethoxy)carbonyl)amino)butanoic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-aminobutanoic acid (11.2 g, 109 mmol) in THF (200 mL) and a 2 M aqueous sodium carbonate solution (65.2 ml, 130 mmol) was added dropwise at 0° C. benzyl carbonochloridate (17.06 mL, 119 mmol). After stirring at room temperature for 16 hours, the reaction mixture was extracted with H2O/TBME, the aqueous layer was acidified with HCl (2M in H2O) until pH=2 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound (22.8 g, 77%) as a colorless oil. The product was used in the next step without further purification. LC-MS: [M−H] 236.2; Rt 0.76 min; (LCMS method 1).

Workup

  1. extractionthe reaction mixture was extracted with H2O/TBME
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5892a1f40a3c4c99bbf73719e397fecb
Source dataset
uspto-grants-2016_03
Patent number
US09296733B2

Reaction notes

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