Potassium Hydroxide → HCID 86602931, compound

HRID 1868173Notes

Reaction equation

HRID 1868173 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:35]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:34]([O:44][C@@H:45]2[O:74][C@H:73]([CH3:75])[C@@H:64]([O:65][CH2:66][C:67]3[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=3)[C@H:55]([O:56][CH2:57][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)[C@H:46]2[O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:33]([CH2:76][O:77][CH2:78][C:79]2[CH:84]=[CH:83][CH:82]=[CH:81][CH:80]=2)[O:32][C@@H:10]1[O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([N:16](C(OC)=O)[O:17][CH2:18]2)[CH2:14][C@H:13]1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C@@H:9]1[C@@H:35]([O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C@H:34]([O:44][C@@H:45]2[O:74][C@H:73]([CH3:75])[C@@H:64]([O:65][CH2:66][C:67]3[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=3)[C@H:55]([O:56][CH2:57][C:58]3[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=3)[C@H:46]2[O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C@@H:33]([CH2:76][O:77][CH2:78][C:79]2[CH:80]=[CH:81][CH:82]=[CH:83][CH:84]=2)[O:32][C@@H:10]1[O:11][C@@H:12]1[C@@H:19]2[C@@H:15]([NH:16][O:17][CH2:18]2)[CH2:14][C@H:13]1[O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 86602929HCID 86602929, compound

Product 1

HCID 86602931HCID 86602931, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

The compound (363 mg, 0.32 mmol) synthesized in Example 6 (6j) was dissolved in methanol (8 mL) and 1N aqueous potassium hydroxide solution (4 mL) was added thereto, followed by stirring of the mixture at 80° C. for 8 hours. After cooling to room temperature, saturated aqueous ammonium chloride solution (15 mL) was added to the reaction mixture and the mixture was extracted with ethyl acetate (100 mL). After the organic layer was washed with saturated brine (10 mL) and dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified using silica gel flash column chromatography (hexane:ethyl acetate, 1.5:1-1:1, V/V) to obtain the desired title compound (313 mg, yield 91%) as pale yellow amorphous matter.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate (100 mL)
  3. washAfter the organic layer was washed with saturated brine (10 mL)
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified

Sources & evidence

ORD record
ord-1825011ebcab42ce9bf01242c0c69146
Source dataset
uspto-grants-2009_12
Patent number
US07632930B2

Reaction notes

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