Hydrochloric Acid → 2(R)-[3,3,3,2,2-pentafluoro-1(S)-(4-fluorophenyl)propylamino]-propionamide
Reaction equation
S[CH2:2][C@H:3]([NH:7][C@@H:8]([C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[C:4](O)=[O:5].[OH-].[Na+].ClCC1C=CC=C[N:28]=1.Cl>>[F:11][C:10]([F:13])([F:12])[C:9]([F:15])([F:14])[C@@H:8]([NH:7][C@H:3]([CH3:2])[C:4]([NH2:28])=[O:5])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1Participants
5
Procedure
To a 0.2 M stock solution of 3-mercapto-2(R)-[2,2,3,3,3-pentafluoro-1-(S)-(4-fluorophenyl)propylamino]-propionic acid in NaOH (10 mL, 2 mmol), 2-chloromethylpyridine (0.328 g, 2 mmol) and 1 N solution of NaOH (1 mL) were added. After stirring the reaction mixture for 5 h at room temperature, 1 M HCl solution was added until pH 5-6. The mixture was extracted with ethyl acetate and the combined organic extracts were washed with brine and dried over sodium sulfate and concentrated to give N-(1-cyanocyclopropyl)-3-pyridin-2-ylmethanesulfanyl)-2(R)-[3,3,3,2,2-pentafluoro-1(S)-(4-fluorophenyl)propylamino]-propionamide as a foam (0.692 g) which was converted to the title compound as described in Example 6 above.
Workup
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic extracts were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-012577685de64488aaa9175962e8712d
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07893093B2
Reaction notes
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