Methanol → HCID 15341810, compound

HRID 893459Notes

Reaction equation

HRID 893459 reaction equation
C[O:2][C:3]([C:5]1(CCC)[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])=[C:22]([OH:33])[C:21]=3[CH2:34][CH:35]=[CH2:36])=[CH:14][C:7]=2[O:6]1)=[O:4].[OH-].[Li+].[CH3:42]O.[CH2:44]1[CH2:48]OC[CH2:45]1>C(OCC)(=O)C>[CH3:42][O:33][C:22]1[C:21]([CH2:34][CH:35]=[CH2:36])=[C:20]([CH:25]=[CH:24][C:23]=1[C:26]([N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)=[O:27])[O:19][CH2:18][CH2:17][CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][CH2:10][CH:5]([C:3]([OH:2])=[O:4])[O:6][C:7]=2[C:14]=1[CH2:45][CH2:44][CH3:48]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 19917189HCID 19917189, compound

Product 1

HCID 15341810HCID 15341810, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The compound of Example 27 (150 mg, 0.27 mmol) and an excess amount of lithium hydroxide were added to 2 to 3 ml of methanol and about I0 ml of THF. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water. Chromatography of the reaction mixture on silica gel with 90% ethyl acetate/9.5% methanol/0.5% 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/9.5% methanol/0.5% acetic acid as eluant gave the product

Sources & evidence

ORD record
ord-3400140cc49342c0b32a9f5f6f033423
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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