Methanol → HCID 25183799, compound

HRID 1925723Notes

Reaction equation

HRID 1925723 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[CH:21]=[CH:20][S:19][C:18]=3[C:22]([O:24]C)=[O:23])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[OH-].[Na+].CO>O1CCCC1>[N:4]1([C:7]2[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]3[CH:21]=[CH:20][S:19][C:18]=3[C:22]([OH:24])=[O:23])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 59180433HCID 59180433, compound

Product 1

HCID 25183799HCID 25183799, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 85 (306 mg; 0.8 mmol) in tetrahydrofuran (2.7 mL) were added aqueous sodium hydroxide (5.3 mL; 2N) and methanol (5.3 mL) sequentially. The reaction mixture was heated at 40° C. for 17 hours, allowed to cool to room temperature, and then extracted with aqueous sodium hydroxide (20 mL; 2N). The aqueous layer was washed with diethyl ether (30 mL×2), acidified with aqueous hydrochloric acid (40 mL; 6N), and extracted with dichloromethane (40 mL). The organic layer was washed with aqueous saturated sodium chloride (20 mL), dried over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting pale yellow solid was recrystallized from hot 80% ethyl acetate in hexane, to yield the title compound as a white solid (53 mg).

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with aqueous sodium hydroxide (20 mL; 2N)
  3. washThe aqueous layer was washed with diethyl ether (30 mL×2)
  4. extractionextracted with dichloromethane (40 mL)
  5. washThe organic layer was washed with aqueous saturated sodium chloride (20 mL)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe resulting pale yellow solid was recrystallized from hot 80% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3a8e15b0f65e42cbbe124f3a441c09cc
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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