Ethanol → HCID 136333088, compound

HRID 915968Notes

Reaction equation

HRID 915968 reaction equation
C(O)C.[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])[CH3:30])(=[O:28])=[O:27])=[CH:22][C:21]=4[O:36][CH3:37])=[N:14][C:13]=3[N:12]([CH3:38])[N:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.[CH3:39][S:40]([OH:43])(=[O:42])=[O:41]>CCOCC>[CH3:39][S:40]([OH:43])(=[O:42])=[O:41].[CH:4]1([C:10]2[C:18]3[C:17](=[O:19])[NH:16][C:15]([C:20]4[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH2:31][CH2:32][N:33]([CH3:34])[CH3:35])[CH3:30])(=[O:28])=[O:27])=[CH:22][C:21]=4[O:36][CH3:37])=[N:14][C:13]=3[N:12]([CH3:38])[N:11]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 136005833HCID 136005833, compound

Product 1

HCID 136333088HCID 136333088, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 1 ml ethanol solution of 44 mg (0.0876 mmol) of the compound obtained in Example 157, 5.8 μl (0.0894 mmol) of methanesulfonic acid was added, and the mixture was heated under reflux for 10 minutes. Then, the reaction mixture was cooled to room temperature, and ether was added to the reaction mixture. Precipitated solids were collected by filtration. The solids were purified by recrystallization (ethyl acetate-ethanol) to obtain 22 mg (42%) of the captioned compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 10 minutes
  3. customPrecipitated solids
  4. filtrationwere collected by filtration
  5. customThe solids were purified by recrystallization (ethyl acetate-ethanol)

Sources & evidence

ORD record
ord-a41d9371675d4fabb462ed3893fd9429
Source dataset
uspto-grants-2007_09
Patent number
US07268128B2

Reaction notes

Loading…