Citric Acid → HCID 137199432, compound

HRID 522209Notes

Reaction equation

HRID 522209 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:27]C)=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=[C:16]([CH2:17][OH:18])[C:9]=23)[CH:7]=1.C([S-])C.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN1CCCC1.[Cl-].[Na+].O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:27])=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:15]=[C:16]([CH2:17][OH:18])[C:9]=23)[CH:7]=1

Participants

6

Reactant 3

HCID 311Citric AcidHCID 4459711Sodium ethanethiolateHCID 131735517HCID 131735517, compound

Product 1

HCID 137199432HCID 137199432, compound

Reagents, catalysts & solvents 2

HCID 84541-MethylpyrrolidineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of Example 14E (920.0 mg, 2.286 mmol) and sodium ethanethiolate (641 mg, 6.86 mmol) in N-methylpyrrolidine (40 mL) was stirred at 120° C. for 3 hours. The mixture was treated with brine, acidified to pH 4-5 with 5% citric acid, and extracted with ethyl acetate (twice). The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, concentrated, and purified on silica using the ISCO Companion flash system eluting with heptanes/ethyl acetate (5:5 to 4:6) to provide the title compound. MS (ESI+) m/z 389.0 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (twice)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica using the ISCO Companion flash system
  7. washeluting with heptanes/ethyl acetate (5:5 to 4:6)

Sources & evidence

ORD record
ord-0e0fa6aed1664fd9a79fd2bc44b446eb
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

Loading…