Potassium Carbonate → HCID 87735051, compound

HRID 902908Notes

Reaction equation

HRID 902908 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH:8]([CH2:12][S:13]C(=O)C)[C:9]([OH:11])=[O:10])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH:8]([CH2:12][SH:13])[C:9]([OH:11])=[O:10])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Procedure

To a stirring solution of the crude compound of example 24 (6.87 g; 26.19 mmoles) in degassed methanol (270 mL) at room temperature was added drop wise a 10% aqueous solution of potassium carbonate (7.24 g; 52.38 mmoles). The mixture was stirred for three hours at room temperature. After complete consumption of the starting material (as confirmed by TLC: 30% ethyl acetate-70% hexanes), the reaction mixture was poured into degassed water (500 mL) and was extracted with degassed dichloromethane (2×200 mL) and then was acidified with a 10% aqueous hydrochloric acid solution. The aqueous layer was finally extracted with ethyl acetate (4×500 mL). The organic extracts were combined, dried (anhydrous MgSO4), filtered and evaporated to yield 8.10 g of the crude desired compound. This residue was used directly in the next step without any further purification.

Workup

  1. customAfter complete consumption of the starting material (as confirmed by TLC: 30% ethyl acetate-70% hexanes)
  2. additionthe reaction mixture was poured
  3. custominto degassed water (500 mL)
  4. extractionwas extracted with degassed dichloromethane (2×200 mL)
  5. extractionThe aqueous layer was finally extracted with ethyl acetate (4×500 mL)
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-debf59bf88d14f2e96f86e1f6dd085a8
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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