Hydrochloric Acid → Hydrochloric Acid

HRID 1638519Notes

Reaction equation

HRID 1638519 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:4][CH:3]1[C:5]([NH:7][C:8](=[CH:16][CH2:17][CH2:18][CH3:19])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:6].[ClH:21].C[CH2:23][O:24]CC>>[CH3:1][C:2]1([CH3:20])[CH2:4][CH:3]1[C:5]([NH:7][C:8]([O:24][CH3:23])([CH:16]=[CH:17][CH2:18][CH3:19])[C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[O:6].[ClH:21]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 53923276HCID 53923276, compound

Product 2

HCID 313Hydrochloric AcidHCID 53863359HCID 53863359, compound

Procedure

A solution of 0.84 g (3.0 mmole) of t-butyl 2-(2,2-dimethylcyclopropanecarboxamido)-2-hexenoate in 10 ml of Et2O saturated with anhydrous HCl was allowed to stand at room temperature under a drying tube. After 17 hrs, the solution was evaporated, and the residual gum was dissolved in 10 ml of saturated NaHCO3. This solution was washed with an additional 15 ml of 0.5N HCl, then dried (MgSO4), filtered, and concentrated to give a viscous oil. The oil was crystallized from toluene. Yield of white crystals=0.32 g (47%), m.p. 119°-122°. TLC (4:1 toluene-AcOH) showed a single spot. NMR indicated essentially pure Z-isomer. (Note: Treatment of the methanol adduct, t-butyl 2-(2,2-dimethylcyclopropanecarboxamido)-2-methoxyhexenoate, with anhydrous HCl in Et2O under similar conditions gave the same product.)

Workup

  1. customto stand at room temperature under a drying tube
  2. customthe solution was evaporated
  3. dissolutionthe residual gum was dissolved in 10 ml of saturated NaHCO3
  4. washThis solution was washed with an additional 15 ml of 0.5N HCl
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a viscous oil
  9. customThe oil was crystallized from toluene

Sources & evidence

ORD record
ord-6124e952f4174f53beaf4b2c1aca6afd
Source dataset
uspto-grants-1989_11
Patent number
US04880793

Reaction notes

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