Methanol → HCID 67076802, compound

HRID 250790Notes

Reaction equation

HRID 250790 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])=[C:6]([C:8]2[C:9]([C:14]([O:16]CC)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1.CO.C1COCC1.[OH-].[Na+]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[O:25][C:26]=2[CH3:27])=[C:6]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 67077055HCID 67077055, compound

Product 1

HCID 67076802HCID 67076802, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the compound obtained in Example 5 (0.128 g; 0.287 mmol), methanol (2.5 ml), THF (5 ml), aqueous 1N sodium hydroxide (0.37 ml; 0.37 mmol) and water (2.5 ml) is stirred at reflux for 1 hour. The medium is then cooled and poured into water. After extracting with ethyl ether, the aqueous phase is acidified with concentrated hydrochloric acid. The white precipitate formed is taken up in ethyl acetate. Evaporation gives a beige-coloured solid (76 mg; 63% yield).

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe medium is then cooled
  3. extractionAfter extracting with ethyl ether
  4. customThe white precipitate formed
  5. customEvaporation
  6. customgives a beige-coloured solid (76 mg; 63% yield)

Sources & evidence

ORD record
ord-50f5f3dc72194a2398995fdf74e7d6a5
Source dataset
uspto-grants-2011_01
Patent number
US07863328B2

Reaction notes

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