Potassium Carbonate → HCID 12967658, compound

HRID 375718Notes

Reaction equation

HRID 375718 reaction equation
C([O:4][C:5]1[CH:6]=[C:7]([O:36]C(=O)C)[C:8]2[CH2:19][S:18][CH2:17][C@@H:16]([C:20]([O:22][CH3:23])=[O:21])[NH:15][C:14](=[O:24])[C@@H:13]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:12][O:11][C:10](=[O:33])[C:9]=2[C:34]=1[CH3:35])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.C(OCC)(=O)C>[OH:4][C:5]1[CH:6]=[C:7]([OH:36])[C:8]2[CH2:19][S:18][CH2:17][C@@H:16]([C:20]([O:22][CH3:23])=[O:21])[NH:15][C:14](=[O:24])[C@@H:13]([NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:12][O:11][C:10](=[O:33])[C:9]=2[C:34]=1[CH3:35]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 54045675HCID 54045675, compound

Product 1

HCID 12967658HCID 12967658, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 32 mg of t-butyl (4R,7S)-12,14-diacetoxy-1,3,4,5,6,7,8,10-octahydro-4-methoxycarbonyl-11-methyl-6,10-dioxo-9,2,5-benzoxathiaazacyclododecine-7-carbamate in 3 ml of methanol were added 15 mg of potassium carbonate. After stirring for 30 minutes at room temperature the reaction mixture was diluted with ethyl acetate and washed consecutively with 0.1M pH 7 aqueous sodium phosphate buffer and with brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was purified by chromatography on silica gel using acetone/n-hexane 1:2 (v/v) as eluent. The purified product was dissolved in methylene chloride and precipitated by slow addition of n-hexane to yield t-butyl (4R,7S)-1,3,4,5,6,7, 8,10-octahydro-12,14-dihydroxy-4-methoxycarbonyl-11-methyl-6,10-dioxo -9,2,5-benzoxathiaazacyclododecine-7-carbamate as a white, amorphous material.

Workup

  1. washwashed consecutively with 0.1M pH 7 aqueous sodium phosphate buffer and with brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by chromatography on silica gel
  5. dissolutionThe purified product was dissolved in methylene chloride
  6. customprecipitated by slow addition of n-hexane

Sources & evidence

ORD record
ord-25e07c7be5224646aea4478d9163efc1
Source dataset
uspto-grants-1996_01
Patent number
US05486466

Reaction notes

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