Hydrochloric Acid → HCID 22901902, compound

HRID 1735989Notes

Reaction equation

HRID 1735989 reaction equation
C(OC([O:6][CH:7]1[C:12]2[CH:13]=[C:14]([S:16]([NH:19][C:20]([CH3:23])([CH3:22])[CH3:21])(=[O:18])=[O:17])[S:15][C:11]=2[S:10](=[O:25])(=[O:24])[N:9](C(OCC)C)[CH2:8]1)C)C.Cl>C1COCC1>[OH:6][CH:7]1[C:12]2[CH:13]=[C:14]([S:16]([NH:19][C:20]([CH3:21])([CH3:22])[CH3:23])(=[O:17])=[O:18])[S:15][C:11]=2[S:10](=[O:25])(=[O:24])[NH:9][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19434048HCID 19434048, compound

Product 1

HCID 22901902HCID 22901902, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the product from Step E (158 g, 0.325 mol), THF (700 mL) and 2N HCl (180 mL) were stirred at room temperature for 20 hr. After evaporating the THF, the aqueous mixture was cooled to 0° C. and sodium bicarbonate (50 g) was carefully added followed by water (400 mL) and ethyl acetate (500 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (250 mL). The combined organic extracts were washed with brine, dried (MgSO4) and evaporated to give a foam which was triturated with methylene chloride (200 mL) to give a solid (81.7 g, 75%): mp 144°-147° C. Recrystallization of this solid from methylene chloride gave an off-white solid: mp 163°-165° C.

Workup

  1. customAfter evaporating the THF
  2. temperaturethe aqueous mixture was cooled to 0° C.
  3. additionsodium bicarbonate (50 g) was carefully added
  4. customThe two layers were separated
  5. extractionthe aqueous layer was extracted with ethyl acetate (250 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a foam which
  10. customwas triturated with methylene chloride (200 mL)

Sources & evidence

ORD record
ord-f13e86aa1547499ea35d5ee6ccdd715c
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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