Methanol → HCID 15157461, compound

HRID 2371628Notes

Reaction equation

HRID 2371628 reaction equation
[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:31][CH2:32][C:33]([OH:35])=[O:34])([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:3]1.[CH2:36]1[O:38][CH:37]1[CH2:39][OH:40].[OH-:41].[CH2:42]([N+](C)(C)C)[C:43]1[CH:48]=CC=CC=1.C[OH:54]>CN(C)C=O.[OH-].C([N+](C)(C)C)C1C=CC=CC=1>[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][C:10]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[C:11]([CH2:12][CH2:13][CH3:14])[C:6]=2[O:5][C:4]([CH2:31][CH2:32][C:33]([O:35][CH2:42][CH:43]([OH:54])[CH2:48][OH:41])=[O:34])([CH2:26][CH2:27][C:28]([O:30][CH2:36][CH:37]([OH:38])[CH2:39][OH:40])=[O:29])[CH2:3]1

Participants

7

Reactant 4

HCID 887MethanolHCID 11164Glycidol2×HCID 66854Benzyltrimethylammonium hydroxideHCID 15157434HCID 15157434, compound

Product 1

HCID 15157461HCID 15157461, compound

Reagents, catalysts & solvents 2

HCID 66854Benzyltrimethylammonium hydroxideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 250 mg (0.515 mmol) of the titled product of Example 17, 153 mg (2.06 mmol) of glycidol, and 9 mg of a 40% solution of benzyl-trimethylammonium hydroxide in methanol in 2.5 ml of dimethyl formamide under argon was stirred overnight at 70° C. After addition of another 153 mg of glycidol and one drop of 40% methanolic benzyltrimethylammonium hydroxide, the temperature was raised to 85°-90° C. with stirring. After stirring for 7 hours, the mixture was permitted to cool and was then partitioned between ethyl acetate and water. The aqueous layer was further extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4), the drying agent removed by filtration, and the solvent removed on a rotary evaporator. The residue was chromatographed on a silica gel column. Elution with 10% methanol/2.5% acetic acid/87.5% ethyl acetate as eluent afforded, after drying under vacuum for eight hours, the title product (170 mg), which was isolated as the hemihydrate.

Workup

  1. temperaturethe temperature was raised to 85°-90° C.
  2. stirringwith stirring
  3. stirringAfter stirring for 7 hours
  4. temperatureto cool
  5. customwas then partitioned between ethyl acetate and water
  6. extractionThe aqueous layer was further extracted twice with ethyl acetate
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. customthe drying agent removed by filtration
  10. customthe solvent removed on a rotary evaporator
  11. customThe residue was chromatographed on a silica gel column
  12. washElution with 10% methanol/2.5% acetic acid/87.5% ethyl acetate as eluent
  13. customafforded
  14. customafter drying under vacuum for eight hours

Sources & evidence

ORD record
ord-8aed3141ba6747bc82ffda8a1d21262d
Source dataset
uspto-grants-1992_03
Patent number
US05093353

Reaction notes

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