Hydrochloric Acid → (2S)-2-{[(Pent-4-en-1-yloxy)carbonyl]amino}non-8-enoic acid

HRID 389178Notes

Reaction equation

HRID 389178 reaction equation
[CH2:1]([O:6][C:7]([NH:9][C@@H:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:11]([O:13]CC)=[O:12])=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5].[Li+].[OH-].Cl>C1COCC1.CCO>[CH2:1]([O:6][C:7]([NH:9][C@@H:10]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:11]([OH:13])=[O:12])=[O:8])[CH2:2][CH2:3][CH:4]=[CH2:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86647499Ethyl (2S)-2-{[(pent-4-en-1-yloxy)carbonyl]amino}non-8-enoate

Product 1

HCID 59571238(2S)-2-{[(Pent-4-en-1-yloxy)carbonyl]amino}non-8-enoic acidYield 91.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl (2S)-2-{[(pent-4-en-1-yloxy)carbonyl]amino}non-8-enoate (0.96 g, 3.08 mmol) in THF (20 mL), EtOH (1 mL) and 1 M aqueous LiOH (21.58 mL, 21.58 mmol) was stirred at RT for 2 hours. The reaction mixture was acidified to pH 5 with 1 N aqueous HCl and extracted with ether (3×100 mL). The combined ether layers were washed with water (100 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to give title compound (0.80 g). LRMS (ESI) m/z 284.4 [(M+H)+; calcd for C15H26NO4: 284.2].

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe combined ether layers were washed with water (100 mL), brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fcfc78e5501749889dfa82f00d83e6f9
Source dataset
uspto-grants-2013_02
Patent number
US08377874B2

Reaction notes

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