Oxalyl chloride → HCID 86666173, compound
Reaction equation
[CH:1]([C@H:4]1[C@@H:8]2[C@@H:9]3[C@@:22]([CH3:25])([CH2:23][CH2:24][C@@:7]2([C:40]([OH:42])=O)[CH2:6][CH2:5]1)[C@@:21]1([CH3:26])[C@@H:12]([C@:13]2([CH3:39])[C@@H:18]([CH2:19][CH2:20]1)[C:17]([CH3:28])([CH3:27])[C@@H:16]([C:29]1[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:30]=1)[CH2:15][CH2:14]2)[CH2:11][CH2:10]3)([CH3:3])[CH3:2].C(Cl)(=O)C([Cl:46])=O>>[Cl:46][C:40]([C@:7]12[CH2:6][CH2:5][C@@H:4]([CH:1]([CH3:3])[CH3:2])[C@@H:8]1[C@@H:9]1[C@@:22]([CH3:25])([CH2:23][CH2:24]2)[C@@:21]2([CH3:26])[C@@H:12]([C@:13]3([CH3:39])[C@@H:18]([CH2:19][CH2:20]2)[C:17]([CH3:27])([CH3:28])[C@@H:16]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([O:37][CH3:38])=[O:36])=[CH:31][CH:30]=2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:42]Participants
3
Procedure
To a flask containing (1S,3aS,5aR,5bR,7aS,9S,11aS,11bR,13aR,13bR)-1-isopropyl-9-(4-(methoxycarbonyl)phenyl)-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysene-3a-carboxylic acid (0.154 g, 0.267 mmol) was added oxalyl chloride (2M in dichloromethane) (5 mL, 10.00 mmol). The solution was stirred at rt for 3 h. The mixture was concentrated under reduced pressure and was dissolved in dichloromethane and concentrated two additional times. The crude product was used in the next step with no additional purification.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- dissolutionwas dissolved in dichloromethane
- concentrationconcentrated two additional times
- customThe crude product was used in the next step with no additional purification
Sources & evidence
- ORD record
- ord-983612fc2bb74adca3ac9db488f87d53
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802661B2
Reaction notes
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