Dichloromethane → (R)-(E)-3-(10-Oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-benzo[f]azulen-6-yl)acrylic acid hydrochloride
Reaction equation
C([O:5][C:6](=[O:24])/[CH:7]=[CH:8]/[C:9]1[CH:10]=[N:11][C:12]2[NH:21][C:20](=[O:22])[C@@H:19]3[N:15]([CH2:16][CH2:17][CH2:18]3)[CH2:14][C:13]=2[CH:23]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:33]>>[ClH:33].[O:22]=[C:20]1[C@@H:19]2[N:15]([CH2:16][CH2:17][CH2:18]2)[CH2:14][C:13]2[CH:23]=[C:9](/[CH:8]=[CH:7]/[C:6]([OH:24])=[O:5])[CH:10]=[N:11][C:12]=2[NH:21]1Participants
Reactant 3
Product 1
Procedure
A solution of (R)-(E)-3-(10-oxo-2,3,4,9,10,10a-hexahydro-1H-3a,8,9-triaza-benzo[f]azulen-6-yl)acrylic acid tert-butyl ester (2.53 g, 7.68 mmol) in CH2Cl2 (15 mL) was treated with TFA (15 mL). After stirring at room temperature under N2 for 45 min, the clear tan solution was concentrated in vacuo. The resulting oil was treated with anhydrous HCl (30 mL of a 4.0 M solution in dioxane, 120 mmol). The resulting mixture was sonicated for 10 min, stirred under N2 for 20 min, diluted with Et2O (100 mL), sonicated for 20 min and stirred for 20 min. The solid was isolated by filtration, washed with Et2O, and dried under vacuum at 50° C. overnight to give the title compound (2.66 g, quantitative) as an off-white solid: MS (ESI) m/e 274 (M+H)+.
Workup
- concentrationthe clear tan solution was concentrated in vacuo
- additionThe resulting oil was treated with anhydrous HCl (30 mL of a 4.0 M solution in dioxane, 120 mmol)
- customThe resulting mixture was sonicated for 10 min
- stirringstirred under N2 for 20 min
- additiondiluted with Et2O (100 mL)
- customsonicated for 20 min
- stirringstirred for 20 min
- customThe solid was isolated by filtration
- washwashed with Et2O
- customdried under vacuum at 50° C. overnight
Sources & evidence
- ORD record
- ord-129a17d6cd054554b41f01b81cff19b8
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879872B2
Reaction notes
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