Potassium Carbonate → HCID 57857006, compound

HRID 561752Notes

Reaction equation

HRID 561752 reaction equation
C1(C2C=CC=CC=2)C=CC(C([O:9][C@@H:10]2[CH2:18][C@@H:13]3[O:14][C:15](=[O:17])[CH2:16][C@@H:12]3[C@H:11]2/[CH:19]=[CH:20]/[C@H:21]([C:23]2[S:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[CH:24]=2)[OH:22])=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO.C1COCC1>[S:27]1[C:23]([C@H:21]([OH:22])/[CH:20]=[CH:19]/[C@@H:11]2[C@@H:12]3[C@@H:13]([O:14][C:15](=[O:17])[CH2:16]3)[CH2:18][C@H:10]2[OH:9])=[CH:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]1=2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57857016HCID 57857016, compound2×

Product 1

HCID 57857006HCID 57857006, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture consisting of (3aR,4R,5R,6aS)-4-((R,E)-3-(benzo[b]thiophen-2-yl)-3-hydroxyprop-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate (intermediate 28, 0.343 g, 0.672 mmol) and potassium carbonate (0.046 g, 0.336 mmol), and 1:1 methanol-THF (12 mL) was stirred at room temperature for 18 hours. The reaction mixture turned from colorless to red-orange. After complete consumption of starting material, as judged by TLC, the reaction mixture was diluted with ethyl acetate (300 mL), washed with 1:1 saturated ammonium chloride-water (2×50 mL) and brine (50 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated to give a yellow solid. The material was triturated in 10% ethyl acetate in hexanes (200 mL) for three days. The product was collected to give an off-white solid which was rinsed with hexanes and dried to afford the title intermediate 29 (189 mg, 85% triturated yield) as an off-white solid; MS (ESI+) m/z 313 (m+H—H2O), (ESI−) m/z 389 (m+AcO−); 1H NMR (d6-DMSO) δ 7.83-7.93 (m, 1H), 7.72-7.83 (m, 1H), 7.24-7.38 (m, 2H), 7.19-7.24 (s, 1H), 5.94-6.01 (m, 1H), 5.65-5.82 (m, 2H), 5.31-5.38 (m, 1H), 4.94-5.01 (m, 1H), 4.84-4.93 (m, 1H), 3.80-3.91 (m, 1H), 2.74-2.88 (m, 1H), 2.56-2.69 (m, 1H), 2.22-2.37 (m, 3H), 1.64-1.80 (m, 1H).

Workup

  1. customAfter complete consumption of starting material
  2. additionthe reaction mixture was diluted with ethyl acetate (300 mL)
  3. washwashed with 1:1 saturated ammonium chloride-water (2×50 mL) and brine (50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customto give a yellow solid
  8. customThe material was triturated in 10% ethyl acetate in hexanes (200 mL) for three days
  9. customThe product was collected
  10. customto give an off-white solid which
  11. washwas rinsed with hexanes
  12. customdried

Sources & evidence

ORD record
ord-0878b8ea8a5542b6a07d1d2a3e65ffe8
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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