Water → HCID 90457444, compound

HRID 625865Notes

Reaction equation

HRID 625865 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1)[C:10]([O:12]C)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[Li+].[OH-]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 51354962HCID 51354962, compound

Product 1

HCID 90457444HCID 90457444, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-fluorophenyl)propanoate (174 mg, 0.524 mmol) in THF (1967 μl)/H2O (656 μl) was added LiOH (37.7 mg, 1.573 mmol) and the reaction was allowed to stir for 2 h. THF was removed by rotovap before the solution was diluted in EtOAc (10 mL) and aqueous phase was acidified to pH 3 using a 1N aqueous HCl solution. The crude product was extracted with EtOAc. The organic fractions were combined and dried over anhydrous sodium sulfate. After filtration and concentration, the crude product, (S)-2-((tert-butoxycarbonyl)amino)-3-(3-chloro-4-fluorophenyl)propanoic acid, was obtained as a yellow gum (0.183 mg, 99%).

Workup

  1. customTHF was removed by rotovap before the solution
  2. additionwas diluted in EtOAc (10 mL)
  3. extractionThe crude product was extracted with EtOAc
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration and concentration

Sources & evidence

ORD record
ord-4870bdd265fa41caa157fc27cdcedb53
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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