Water → (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoic acid

HRID 78739Notes

Reaction equation

HRID 78739 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:16][CH:17]([CH3:19])[CH3:18])/[CH:10]=[CH:11]/[C:12]([O:14]C)=[O:13])=[O:7])([CH3:4])[CH3:3].O.[Li+].[OH-]>C1COCC1.CO>[CH3:4][C:2]([O:5][C:6]([NH:8][C@@H:9]([CH2:16][CH:17]([CH3:19])[CH3:18])/[CH:10]=[CH:11]/[C:12]([OH:14])=[O:13])=[O:7])([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 14081309methyl (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoate

Product 1

HCID 14081310(2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoic acidYield 99.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl (2E,4S)-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-6-methyl-2-heptenoate (5.00 g, 18.43 mmol) in THF (15 mL), MeOH (15.0 mL), and water (15 mL) was added LiOH (2.206 g, 92.00 mmol). After stirring for 2 h at RT, the reaction mixture was concentrated in vacuo. The reaction mixture was acidified with 6 M aq. HCl to pH=5 and then extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered, and concentrated in vacuo to afford the title compound (4.7 g, 99%) as a white semi-solid. LC-MS m/z 158 (M+H-Boc)+, 0.94 min (ret time).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82ba2552cd6d41f785292e0fe76ab612
Source dataset
uspto-grants-2014_09
Patent number
US08841463B2

Reaction notes

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