Trifluoroacetic acid → D-Homophenylalanine Quinoline-3-amide
Reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH2:13])=[O:12])[CH:2]=1.C([NH:21][C@@H:22]([C:31]([OH:33])=[O:32])[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH2:13])=[O:12])[CH:2]=1.[NH2:21][C@@H:22]([C:31]([OH:33])=[O:32])[CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1Participants
3
Procedure
N-Boc-D-homophenylalanine Quinoline-3-amide (2.6 g, 6.42 mmol, procedure 1A) was treated with trifluoroacetic acid (15 mL) at 25° C. for 1 hr. The solution was concentrated to dryness and treated with diethyl ether (10 mL). The solid was filtered and dried. It was dissolved in water (180 mL) and neutralized to pH=7.5 with saturated solution of sodium bicarbonate. The mixture was stirred for 1 hr and the solid was filtered and dried giving the title compound (1.30 g) as white solid.
Workup
- concentrationThe solution was concentrated to dryness
- additiontreated with diethyl ether (10 mL)
- filtrationThe solid was filtered
- customdried
- dissolutionIt was dissolved in water (180 mL)
- filtrationthe solid was filtered
- customdried
Sources & evidence
- ORD record
- ord-c4bb7716b28944f6bfa78d5135ac3611
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879795B2
Reaction notes
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