Hydrochloric Acid → N-[(pent-4-en-1-yloxy)carbonyl]-norleucine

HRID 1095286Notes

Reaction equation

HRID 1095286 reaction equation
[CH2:1]([O:6][C:7]([NH:9][C@H:10]([C:15]([O:17]C)=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5].[OH-].[Na+].Cl>C1COCC1>[CH2:1]([O:6][C:7]([NH:9][C@H:10]([C:15]([OH:17])=[O:16])[CH2:11][CH2:12][CH2:13][CH3:14])=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 45378375methyl N-[(pent-4-enyloxy)carbonyl]-norleucinate

Product 1

HCID 45378373N-[(pent-4-en-1-yloxy)carbonyl]-norleucineYield 88.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl N-[(pent-4-enyloxy)carbonyl]-L-norleucinate (8.50 g, 33.03 mmol) in THF (20 mL) was added 1N NaOH (20 mL). This reaction solution was stirred at RT for 3 hours, then acidified to pH 3 with 1N HCl and extracted with (3×250 mL) EtOAc. The combined EtOAc layer was washed with 50 mL water, 50 mL brine, dried over Na2SO4, filtered and concentrated to give 7.09 g (88%) of the title product as clear oil. LRMS (ESI) m/z 244 [(M+H)+, calcd for C12H22NO4: 244].

Workup

  1. extractionextracted with (3×250 mL) EtOAc
  2. washThe combined EtOAc layer was washed with 50 mL water, 50 mL brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f5d4b1b29432428bb9ecfeb31912e1bd
Source dataset
uspto-grants-2012_03
Patent number
US08138164B2

Reaction notes

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