Potassium Carbonate → HCID 86750109, compound

HRID 1082156Notes

Reaction equation

HRID 1082156 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][C@@H:13](OC(=O)C)[O:12][C:11](=[O:23])[C:10]2[C:24]([CH3:31])=[C:25]([O:29][CH3:30])[CH:26]=[C:27]([OH:28])[C:9]=2[CH:8](C)[S:7][CH2:6]1)=[O:4].[C:33](=O)([O-])[O-:34].[K+].[K+]>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C@H:5]1[NH:17][C:16](=[S:18])[CH2:15][CH2:14][C@@H:13]([CH2:33][OH:34])[O:12][C:11](=[O:23])[C:10]2[C:24]([CH3:31])=[C:25]([O:29][CH3:30])[CH:26]=[C:27]([OH:28])[C:9]=2[CH2:8][S:7][CH2:6]1)=[O:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86750110HCID 86750110, compound

Product 1

HCID 86750109HCID 86750109, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 24 mg of the product of Example 11 and 8.3 mg of potassium carbonate in 0.5 ml of methanol was stirred at room temperature for 2 h. The mixture was diluted with ethyl acetate and washed successively with 1N hydrochloric acid and with water. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residue was crystallized from ethyl acetate/hexane to yield 16 mg of (4R,9S)-15-hydroxy-9-hydroxymethyl-13-methoxy-12-methyl-11-oxo-6-thioxo-3,4,5,6,7,8,9,11-octahydro-1H-10,2,5-benzoxathiaazacyclotridecine-4-carboxylic acid methyl ester as a white solid.

Workup

  1. washwashed successively with 1N hydrochloric acid and with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d483ab779dc841288c7daff9abd832d7
Source dataset
uspto-grants-1996_12
Patent number
US05589473

Reaction notes

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