Methanol → HCID 57835786, compound

HRID 731178Notes

Reaction equation

HRID 731178 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[CH:19]=[CH:18][C:17]([CH:20]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH2:21][C:22]([O:24]C)=[O:23])=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].CO>C1COCC1>[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([O:13][C:14]3[CH:15]=[CH:16][C:17]([CH:20]([C:26]4[S:27][CH:28]=[CH:29][CH:30]=4)[CH2:21][C:22]([OH:24])=[O:23])=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 57835746HCID 57835746, compound

Product 1

HCID 57835786HCID 57835786, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 30 (0.048 g, 0.11 mmol) was added to a 1-dram vial and dissolved in a minimal amount of anhydrous THF. An aqueous solution of lithium hydroxide (2 M, 0.3 mL) was added to the vial. MeOH was added dropwise until the layers were miscible. The vial was sealed and placed on a rotating wheel overnight (18 hours). When the reaction was complete, the solvent was concentrated under a flow of nitrogen until only water was left. The mixture was diluted by the addition of ˜1 mL of water. Hydrochloric acid (3 N aqueous solution) was added dropwise until the pH reached 2. The aqueous solution was extracted with DCM, and the organic layer was dried and concentrated. Flash column chromatography with 0 to 100% EtOAc/hexanes as the eluant and HPLC of the residue afforded 31 as a white film. MS ESI (pos.) m/e: 407.2 (M+H). 1H NMR (400 MHz) (CDCl3) δ 7.35-7.2 (m, 7H); 7.17 (dd, J=5.1, 1.0 Hz, 1H); 6.93-6.73 (m, 4H); 4.72 (m, 1H); 4.61 (m, 1H); 3.16 (dd, J=15.9, 7.6 Hz, 1H); 3.07 (dd, J=15.9, 7.9); 2.61 (m, 1H); 2.19 (m, 2H); 2.02-1.95 (m, 2H); 1.73-1.61 (m, 4H); 0.91-0.69 (m, 2H).

Workup

  1. customThe vial was sealed
  2. customplaced on a rotating wheel overnight (18 hours)
  3. concentrationthe solvent was concentrated under a flow of nitrogen until only water
  4. waitwas left
  5. additionThe mixture was diluted by the addition of ˜1 mL of water
  6. additionHydrochloric acid (3 N aqueous solution) was added dropwise until the pH
  7. extractionThe aqueous solution was extracted with DCM
  8. customthe organic layer was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-0c8f4ba3d23e4ee891009291a5fefe5f
Source dataset
uspto-grants-2009_09
Patent number
US07582803B2

Reaction notes

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