Acetyl chloride → HCID 67748007, compound
Reaction equation
C([NH:11][C@H:12]([C:16]([NH:18][CH:19]([C:23]([F:53])([F:52])[C:24](=[O:51])[CH:25]([NH:33][C:34](=[O:50])[C@H:35]([CH2:47][O:48][CH3:49])[NH:36][C:37]([O:39]CC1C=CC=CC=1)=O)[CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:13][O:14][CH3:15])(OCC1C=CC=CC=1)=O.[CH2:54](N(CC)CC)C.[C:61](Cl)(=[O:63])[CH3:62]>C(Cl)Cl.[Pd]>[C:61]([NH:11][C@H:12]([C:16]([NH:18][CH:19]([C:23]([F:52])([F:53])[CH:24]([OH:51])[CH:25]([NH:33][C:34](=[O:50])[C@H:35]([CH2:47][O:48][CH3:49])[NH:36][C:37](=[O:39])[CH3:54])[CH2:26][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)[CH:20]([CH3:21])[CH3:22])=[O:17])[CH2:13][O:14][CH3:15])(=[O:63])[CH3:62]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution was 50 mg of the resultant compound of Example 185 and 20 mg of 10% Pd/C was stirred vigorously under a hydrogen atmosphere. After 30 minutes, the catalyst was filtered off and the filtrate concentrated to give a colorless oil, which was dissolved in 2 ml of CH2Cl2. The solution was cooled to 0° C., 0.03 ml of triethylamine and 0.01 ml of acetyl chloride was added. After 2 hrs, the solution was concentrated and the crude product purified by silica gel column chromatography (5% MeOH/CH2Cl2) to give 16 mg of the desired compound. Mass spectrum: (M+H)+ =565.
Workup
- filtrationthe catalyst was filtered off
- concentrationthe filtrate concentrated
- customto give a colorless oil, which
- waitAfter 2 hrs
- concentrationthe solution was concentrated
- customthe crude product purified by silica gel column chromatography (5% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-b5afff4a834b4bf5b89cee8dd3320dbd
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05142056
Reaction notes
Loading…