(2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester → (2S,4R)-1-(1-Carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid
Reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:15][C@@H:14]([F:16])[CH2:13][N:12]1[C:17](=[O:31])[NH:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28](=[O:30])[NH2:29])[CH:20]=1)=[O:10])C1C=CC=CC=1>C1COCC1.[Pd]>[C:28]([N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:18][C:17]([N:12]2[CH2:13][C@H:14]([F:16])[CH2:15][C@H:11]2[C:9]([OH:10])=[O:8])=[O:31])=[CH:20]1)(=[O:30])[NH2:29]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (2S,4R)-1-(1-carbamoyl-1H-indol-3-ylcarbamoyl)-4-fluoro-pyrrolidine-2-carboxylic acid benzyl ester (2.5 g, 5.89 mmol) in THF (40 mL) was added Pd/C 10% (500 mg). Air was removed from the flask under high vacuum and replaced with nitrogen, this operation was repeated three times and finally nitrogen was removed and replaced with hydrogen. The mixture was stirred under a hydrogen atmosphere for 16 h. Hydrogen was removed under vacuum and replaced with nitrogen and the catalyst was removed by filtration over a pad of Celite and washed with THF. Solvents were concentrated to give the title product. MS (LC/MS): 335.0 [M+H]+, 691.2 [2M+Na]+, 333.1 [M−H]−; tR (HPLC conditions a): 2.22 min.
Workup
- customAir was removed from the flask under high vacuum
- customwas removed
- customHydrogen was removed under vacuum
- customthe catalyst was removed by filtration over a pad of Celite
- washwashed with THF
- concentrationSolvents were concentrated
Sources & evidence
- ORD record
- ord-8caf71949da14e12b675730c2e307b7a
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09085555B2
Reaction notes
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