Hydrochloric Acid → HCID 131435015, compound

HRID 1623087Notes

Reaction equation

HRID 1623087 reaction equation
C(S([NH:7][CH:8]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]([CH3:17])([CH3:16])[C:11](OCC)=[O:12])=O)(C)(C)C.Cl.C(N(CC)CC)C.C1(C)C=CC=CC=1.C[OH:40]>>[CH3:16][C:10]1([CH3:17])[C:9](=[O:40])[CH:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[NH:7][C:11]1=[O:12]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1140TolueneHCID 8471Triethylamine2×HCID 66686029HCID 66686029, compound

Product 1

HCID 131435015HCID 131435015, compound

Conditions

Temperature
100 °C

Procedure

To a stirred solution of Ethyl 4-[(tert-butylsulfinyl)amino]-2,2-dimethyl-4-phenylbutanoate from Step B (0.19 g, 0.55 mmol) in MeOH (10 mL) was added anhydrous HCl (gas, bubbled in for about 1 minute). After 20 minutes, nitrogen was bubbled though the reaction mixture for about 20 minutes. The initial solvent was removed in vacuo, and then more MeOH was added and removed in vacuo. The residue was then dissolved in MeOH (20 mL) and treated with triethylamine (0.22 g, 2.2 mmol). The solvent was once again removed in vacuo. This residue was then treated with toluene (10 mL) and triethylamine (0.22 g, 2.2 mmol) before being heated to 100° C. for 15 hours. After cooling to ambient temperature the solvent was removed in vacuo and the residue was partitioned between diethyl ether (50 mL) and 1 M HCl (50 mL). The organics were then successively washed with another volume of 1 M HCl, water and lastly saturated brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound which was used without further purification. MS: m/z=190 (M+1).

Workup

  1. customnitrogen was bubbled though the reaction mixture for about 20 minutes
  2. customThe initial solvent was removed in vacuo
  3. additionmore MeOH was added
  4. customremoved in vacuo
  5. dissolutionThe residue was then dissolved in MeOH (20 mL)
  6. customThe solvent was once again removed in vacuo
  7. temperatureAfter cooling to ambient temperature the solvent
  8. customwas removed in vacuo
  9. customthe residue was partitioned between diethyl ether (50 mL) and 1 M HCl (50 mL)
  10. washThe organics were then successively washed with another volume of 1 M HCl, water and lastly saturated brine
  11. dry with materialThe organic layer was dried over Na2SO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dcb3f0d4585245cea2a9240fee594759
Source dataset
uspto-grants-2014_07
Patent number
US08778957B2

Reaction notes

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