Potassium Carbonate → 11-Acetyl-4-formyl-9-hydroxy-6-methoxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-8-ylmethyl carbamate

HRID 236589Notes

Reaction equation

HRID 236589 reaction equation
[C:1](=[O:26])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[N:15]3[C:20](=[O:22])[CH3:21])[C:11]2[C:6]1=[C:7]([OH:25])[CH:8]=[C:9]([CH:23]=[O:24])[CH:10]=2)[NH2:2].[C:27](=O)([O-])[O-].[K+].[K+]>CC(C)=O.CI>[C:1](=[O:26])([O:3][CH2:4][CH:5]1[C:17]2([OH:19])[O:18][N:12]([CH2:13][CH:14]3[CH:16]2[N:15]3[C:20](=[O:22])[CH3:21])[C:11]2[C:6]1=[C:7]([O:25][CH3:27])[CH:8]=[C:9]([CH:23]=[O:24])[CH:10]=2)[NH2:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 3035469FR 66980

Product 1

HCID 990772711-Acetyl-4-formyl-9-hydroxy-6-methoxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12]tetradeca-2,4,6-trien-8-ylmethyl carbamateYield 19.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6328Methyl iodideSolvent

Conditions

Temperature
45 °C

Procedure

11-Acetyl-4-formyl-6,9-dihydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (55 mg) was dissolved in a mixture of acetone (2 ml) and methyl iodide (2 ml). To the solution was added potassium carbonate (150 mg), and the mixture was stirred at 45° C. overnight under nitrogen atmosphere. The mixture was cooled to room temperature and filtered, and the filter cake was washed with a mixture of chloroform and acetone (1:1, v/v, 10 ml). The filtrate and the washings were combined and evaporated in vacuo. The residue was subjected to column chromatography on silica gel, and elution was carried out with a mixture of chloroform and acetone (4:1, v/v). The desired fractions were collected and evaporated to dryness. The residue was subjected to preparative thin layer chromatography, which was developed with a mixture of chloroform and methanol (1:1, v/v) to afford 11-acetyl-4-formyl-9-hydroxy-6-methoxy-14-oxa-1,11-diazatetracyclo[7.4.1.02,7.010,12 ]tetradeca-2,4,6-trien-8-ylmethyl carbamate (11 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. washthe filter cake was washed with a mixture of chloroform and acetone (1:1, v/v, 10 ml)
  4. customevaporated in vacuo
  5. washThe residue was subjected to column chromatography on silica gel, and elution
  6. additionwas carried out with a mixture of chloroform and acetone (4:1
  7. customThe desired fractions were collected
  8. customevaporated to dryness
  9. additionwas developed with a mixture of chloroform and methanol (1:1

Sources & evidence

ORD record
ord-0e7370df7726493d9a546d9a9f09d470
Source dataset
uspto-grants-1987_02
Patent number
US04645765

Reaction notes

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