Sodium Hydroxide → (S)-2-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyrylamino)-propionic acid

HRID 44146Notes

Reaction equation

HRID 44146 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-:17].[Na+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=[O:17])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 2734668(S)-2-((tert-Butoxycarbonyl)amino)-3,3-dimethylbutanoic acid

Product 1

HCID 86674881(S)-2-((S)-2-tert-Butoxycarbonylamino-3,3-dimethyl-butyrylamino)-propionic acidYield 191.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)-3,3-dimethylbutanoic acid (18) (6.5 g, 19.7 mmol) in THF (30 mL) was added NaOH (1.7 g, 43.8 mmol) in H2O (60 mL) and the reaction mixture stirred at ambient temperature for 16 h. THF was subsequently removed in vacuo and the aqueous phase washed with EtOAc (50 mL). The aqueous phase was then adjusted to pH ˜2 by addition of 1M HCl and extracted with EtOAc (3×50 mL). The organics were combined dried over MgSO4 and evaporated to give the desired compound (20) as a white solid (5.7 g, 95%); AnalpH2_MeOH; Rt 2.61 min; m/z 303 (MH+); white solid

Workup

  1. customTHF was subsequently removed in vacuo
  2. washthe aqueous phase washed with EtOAc (50 mL)
  3. additionThe aqueous phase was then adjusted to pH ˜2 by addition of 1M HCl
  4. extractionextracted with EtOAc (3×50 mL)
  5. dry with materialThe organics were combined dried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-8538f27e322f45068c5ac77bf9d37850
Source dataset
uspto-grants-2013_09
Patent number
US08541363B2

Reaction notes

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