Methanethiol → HCID 13505578, compound

HRID 2290391Notes

Reaction equation

HRID 2290391 reaction equation
[CH3:1][SH:2].C[O-].[Na+].Br[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]/[CH:12]=[C:13](\[NH:17][C:18]([CH:20]1[CH2:22][C:21]1([CH3:24])[CH3:23])=[O:19])/[C:14]([OH:16])=[O:15].N#N>CO>[CH3:23][C:21]1([CH3:24])[CH2:22][CH:20]1[C:18]([NH:17]/[C:13](=[CH:12]\[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][S:2][CH3:1])/[C:14]([OH:16])=[O:15])=[O:19]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 947NitrogenHCID 10942334Sodium MethoxideHCID 13505574HCID 13505574, compound

Product 1

HCID 13505578HCID 13505578, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stream of CH3SH gas was bubbled through a solution of 162 mg (3 mmoles) of sodium methoxide in 5 ml of methanol for 10 min. with cooling in an ice bath. The solution was allowed to warm to room temperature and 332 mg (1 mmole) of Z-8-bromo-2-(2,2-dimethylcyclopropanecarboxamido)-2-octenoic acid was added. The solution was heated under reflux for 30 min. in a N2 atmosphere. Most of the methanol was evaporated under reduced pressure, the residue 2.5 N HCl. The precipitated oil was extracted with ether (3×). The ether extracts were washed with water, saturated brine and dried over MgSO4. Removal of the ether under reduced pressure gave a colorless oil that crystallized upon standing. It was recrystallized from ether-hexane to give 178 mg of Z-2-(2,2-dimethylcyclopropanecarboxamido)-8-methylthio-2-octenoic acid, m.p. 82°-84° C. Homogeneous by TLC (toluene-acetic acid, 4:1). The NMR spectrum was in accord with the desired structure

Workup

  1. temperaturewith cooling in an ice bath
  2. temperatureThe solution was heated
  3. customMost of the methanol was evaporated under reduced pressure
  4. extractionThe precipitated oil was extracted with ether (3×)
  5. washThe ether extracts were washed with water, saturated brine
  6. dry with materialdried over MgSO4
  7. customRemoval of the ether under reduced pressure
  8. customgave a colorless oil that
  9. customcrystallized
  10. customIt was recrystallized from ether-hexane

Sources & evidence

ORD record
ord-ee3b9f20858c42269d47e19521e262ea
Source dataset
uspto-grants-1986_10
Patent number
US04616038

Reaction notes

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