Hydrochloric Acid → HCID 58381689, compound

HRID 410059Notes

Reaction equation

HRID 410059 reaction equation
CC[O-].[Na+].[SH:5][C:6]([CH2:12][CH3:13])([CH2:10][CH3:11])[C:7]([OH:9])=[O:8].CS(O[CH2:19][CH2:20][CH2:21][CH2:22]/[CH:23]=[CH:24]\[CH2:25]/[CH:26]=[CH:27]\[CH2:28]/[CH:29]=[CH:30]\[CH2:31]/[CH:32]=[CH:33]\[CH2:34]/[CH:35]=[CH:36]\[CH2:37][CH3:38])(=O)=O.[NH4+].[Cl-].Cl>CCO>[CH2:10]([C:6]([S:5][CH2:38][CH2:37][CH2:36][CH2:35]/[CH:34]=[CH:33]\[CH2:32]/[CH:31]=[CH:30]\[CH2:29]/[CH:28]=[CH:27]\[CH2:26]/[CH:25]=[CH:24]\[CH2:23]/[CH:22]=[CH:21]\[CH2:20][CH3:19])([CH2:12][CH3:13])[C:7]([OH:9])=[O:8])[CH3:11]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 2723922Sodium ethoxideHCID 9855516HCID 9855516, compoundHCID 58381726HCID 58381726, compound

Product 1

HCID 58381689HCID 58381689, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

NaOEt (21 wt. % in EtOH, 0.37 mL, 0.98 mmol) was added dropwise to a solution of 2-mercapto-2-ethyl butyric acid (0.08 g, 0.49 mmol) in dry EtOH (7 mL) held at 0° C. under inert atmosphere. The resulting mixture was stirred at 0° C. for 30 minutes before a solution of (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenyl methanesulfonate (0.15 g, 0.41 mmol) in dry EtOH (3 mL) was added dropwise. The resulting turbid mixture was stirred at ambient temperature for 24 hours, poured into NH4Cl (sat.)(aq.) (15 mL), added 3M HCl to pH ˜2 before extracted twice with EtOAc (2×20 mL). The combined organic extracts were washed with brine (10 mL), dried (MgSO4), filtrated and evaporated in vacuo. The residue was purified by flash chromatography on silica gel using a gradient of 10-25% ethyl acetate in heptane as eluent. Concentration of the appropriate fractions afforded 0.12 g (70% yield) of the title compound as oil.

Workup

  1. customheld at 0° C. under inert atmosphere
  2. additionwas added dropwise
  3. extractionbefore extracted twice with EtOAc (2×20 mL)
  4. washThe combined organic extracts were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltrated
  7. customevaporated in vacuo
  8. customThe residue was purified by flash chromatography on silica gel using a gradient of 10-25% ethyl acetate in heptane as eluent

Sources & evidence

ORD record
ord-5edae83ee9d545568a29c0565f363ba9
Source dataset
uspto-grants-2014_06
Patent number
US08759558B2

Reaction notes

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