Ammonium Hydroxide → Cis-2-Methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarboxamide
Reaction equation
[CH3:1][CH:2]1[CH:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][N:3]1[C:17](Cl)=[O:18].[OH-].[NH4+:21]>O1CCCC1.O>[CH3:1][C@H:2]1[C@@H:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=2)[CH2:4][N:3]1[C:17]([NH2:21])=[O:18]Participants
5
Procedure
A solution of 4.02 g (0.01 mole) of crude (73%) 2-methyl-3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride cis isomer in 20 ml of tetrahydrofuran was treated while stirring with 2 ml (0.02 mole) of 57% aqueous ammonium hydroxide. After stirring for 6 hr, the reaction mixture was diluted with 100 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The combined extracts were dried over magnesium sulfate and concentrated in vacuo to give 4.2 g. A sample of the oil crystallized at -78° C. and was used to seed the bulk of the material. The resulting solid was recrystallized from benzene/isooctane to yield 2.35 g (87%) of white crystalline product, m.p. 107°-108° C.
Workup
- additionwas treated
- customthe oil which separated
- extractionwas extracted into methylene chloride (2×50 ml)
- dry with materialThe combined extracts were dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customto give 4.2 g
- customA sample of the oil crystallized at -78° C.
- customThe resulting solid was recrystallized from benzene/isooctane
Sources & evidence
- ORD record
- ord-7da27c067bdf4e1d9d9d2f4ec953aefe
- Source dataset
- uspto-grants-1990_09
- Patent number
- US04956359
Reaction notes
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