Hydrochloric Acid → N-Hept-6-enoyl-3-methyl-L-valine

HRID 389180Notes

Reaction equation

HRID 389180 reaction equation
[C:1]([NH:9][C@H:10]([C:15]([O:17]C)=[O:16])[C:11]([CH3:14])([CH3:13])[CH3:12])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7].Cl>C1COCC1.[OH-].[Na+]>[C:1]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[C:11]([CH3:12])([CH3:13])[CH3:14])(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]=[CH2:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59571176Methyl N-Hept-6-enoyl-3-methyl-L-valinate

Product 1

HCID 59571200N-Hept-6-enoyl-3-methyl-L-valineYield 84.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of methyl N-hept-6-enoyl-3-methyl-L-valinate (1.40 g, 5.48 mmol) in THF (10 mL) and 1N NaOH (10 mL) was stirred at RT for 2 hours. The reaction mixture was acidified to pH 3 with 1 N HCl and extracted with EtOAc (3×150 mL). The combined organic phases were washed with water (50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to give the title compound (1.12 g). LRMS (ESI) m/z 242.3 [(M+H)+; calcd for C13H24NO3: 242.2].

Workup

  1. extractionextracted with EtOAc (3×150 mL)
  2. washThe combined organic phases were washed with water (50 mL), brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a74246366342568dba09263edf5108
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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