Hydrochloric Acid → 2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acid

HRID 1443492Notes

Reaction equation

HRID 1443492 reaction equation
[Li+].[OH-:2].[CH2:3]([N:9]([CH3:20])[C:10]([CH:12]1[CH2:17][CH:16]2[CH2:18][CH:13]1[C:14](=[O:19])[O:15]2)=[O:11])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8].Cl>>[CH2:3]([N:9]([CH3:20])[C:10]([CH:12]1[CH2:17][CH:16]([OH:15])[CH2:18][CH:13]1[C:14]([OH:2])=[O:19])=[O:11])[CH2:4][CH2:5][CH2:6][CH:7]=[CH2:8]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 591654883-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid hex-5-enyl-methylamide

Product 1

HCID 684256202-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarboxylic acidYield 88%

Procedure

A solution of LiOH (105 mg in 4 mL, of water) was added at 0° C. to the lactone amide (65). After 1 h, the conversion was completed (HPLC). The mixture was acidified to pH 2-3 with 1N HCl, extracted with EtOAc, dried (MgSO4), evaporated, co-evaporated with toluene several times, and dried under high vacuum overnight to give the title compound (520 mg, 88%), m/z=270 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (MgSO4)
  3. customevaporated, co-evaporated with toluene several times
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-4c66123603d54b5bb32d131cfa30455e
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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