Methanol → HCID 15817161, compound

HRID 1033640Notes

Reaction equation

HRID 1033640 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:35][CH2:36][CH3:37])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]([NH:33][CH3:34])=[O:32])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27].[OH-].[Li+].CO.C1COCC1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:4]([CH2:35][CH2:36][CH3:37])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]([NH:33][CH3:34])=[O:32])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 15341815HCID 15341815, compound

Product 1

HCID 15817161HCID 15817161, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 34 (70 mg, 0.14 mmol) and excess 1.0M lithium hydroxide solution were added to about 2 ml of methanol and about 1 ml of THF. The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate and washed with water. Chromatography of the reaction mixture on silica gel with 90% ethyl acetate/10% methanol/trace amount of acetic acid as eluant gave the product.

Workup

  1. washwashed with water
  2. customChromatography of the reaction mixture on silica gel with 90% ethyl acetate/10% methanol/trace amount of acetic acid as eluant gave the product

Sources & evidence

ORD record
ord-4a639b0df5b549d7a58d01945cfa3a47
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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