Methanol → HCID 15237280, compound

HRID 1033630Notes

Reaction equation

HRID 1033630 reaction equation
[CH:1]1([CH2:4][C:5]2[C:32]([O:33][CH3:34])=[C:31]([C:35]([NH:37][CH3:38])=[O:36])[CH:30]=[CH:29][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]3[CH2:16][CH2:17][CH:18]([C:20]([O:22]C)=[O:21])[O:19][C:14]=3[C:13]=2[CH2:26][CH2:27][CH3:28])[CH2:3][CH2:2]1.CO.O.C(OCC)(=O)C>[OH-].[Li+].C(O)(=O)C>[CH:1]1([CH2:4][C:5]2[C:32]([O:33][CH3:34])=[C:31]([C:35]([NH:37][CH3:38])=[O:36])[CH:30]=[CH:29][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]3[CH2:16][CH2:17][CH:18]([C:20]([OH:22])=[O:21])[O:19][C:14]=3[C:13]=2[CH2:26][CH2:27][CH3:28])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 8857Ethyl AcetateHCID 15237279HCID 15237279, compound

Product 1

HCID 15237280HCID 15237280, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

The compound of Example 18 (20 mg, 0.038 mmol) was added to 2 drops of 1M lithium hydroxide, about 2 ml of methanol and 1.0 ml of water. The reaction mixture was stirred overnight at room temperature then washed with water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated to yield the crude product. Chromatography of the crude product on silica gel with 90% ethyl acetate, 10% methanol and a trace amount of acetic acid as eluant gave the product.

Workup

  1. washthen washed with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto yield the crude product

Sources & evidence

ORD record
ord-811eae1f0b1a41ff920caded2f5b5ec4
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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