Hydrochloric Acid → N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valine

HRID 1924380Notes

Reaction equation

HRID 1924380 reaction equation
[CH2:1]([C:5]1[O:9][C:8]([NH:10][C@H:11]([C:15]([O:17]C)=[O:16])[CH:12]([CH3:14])[CH3:13])=[N:7][N:6]=1)[CH2:2][CH:3]=[CH2:4].[Li+].[OH-].Cl>O.C1COCC1>[CH2:1]([C:5]1[O:9][C:8]([NH:10][C@H:11]([C:15]([OH:17])=[O:16])[CH:12]([CH3:14])[CH3:13])=[N:7][N:6]=1)[CH2:2][CH:3]=[CH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67519434methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate

Product 1

HCID 44549470N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valine

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a 0.18 M solution of methyl N-(5-but-3-en-1-yl-1,3,4-oxadiazol-2-yl)-L-valinate (from Step 4) in H2O/THF (1/1 v/v), LiOH (2 eq.) was added at RT. The resulting reaction mixture was stirred for 1 h at RT and then treated with HCl 1N until pH=2 was reached. The aqueous phase was extracted with EtOAc and the organic layer dried over Na2SO4 to obtain a pale yellow solid. MS (ES+) C11H17N3O3 requires: 239 found: 240 (M+H+).

Workup

  1. customThe resulting reaction mixture
  2. extractionThe aqueous phase was extracted with EtOAc
  3. dry with materialthe organic layer dried over Na2SO4
  4. customto obtain a pale yellow solid

Sources & evidence

ORD record
ord-cc7610ffd03248af969843186c05a6da
Source dataset
uspto-grants-2012_05
Patent number
US08178520B2

Reaction notes

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