Methanol → (S)-tert-butyl 3-amino-4-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-4-oxobutanoate
Reaction equation
C1C2C(COC([NH:18][C@H:19]([C:28]([N:30]([C@@H:42]([CH3:50])[CH:43]([O:47][CH2:48][CH3:49])[O:44][CH2:45][CH3:46])[CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[C:36]4[C:41]=3[N:40]=[CH:39][CH:38]=[CH:37]4)=[O:29])[CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.CC(=O)OCC.CO>C(Cl)Cl>[NH2:18][C@H:19]([C:28]([N:30]([C@@H:42]([CH3:50])[CH:43]([O:47][CH2:48][CH3:49])[O:44][CH2:45][CH3:46])[CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[C:36]2[C:41]=1[N:40]=[CH:39][CH:38]=[CH:37]2)=[O:29])[CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-tert-Butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(((S)-1,1-diethoxypropan-2-yl)(quinolin-8-ylmethyl)amino)-4-oxobutanoate (Compound III-17) 18.4 g (27 mmol) and piperidine 22.7 g (270 mmol) were added in DCM (90 ml). The mixture was stirred for 1.5 h at room temperature. The mixture was diluted with DCM (200 ml) and washed with water (150 ml×3). The solution was concentrated in vacuo. The residue was purified by column chromatography on silica gel with PE:EA=50:1 to DCM:MeOH=10:1 to give the title compound 10.5 g, (yield 85%).
Workup
- washwashed with water (150 ml×3)
- concentrationThe solution was concentrated in vacuo
- customThe residue was purified by column chromatography on silica gel with PE
Sources & evidence
- ORD record
- ord-5bd4b0420ddd41ce86fcaaf2ffc9db4b
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09193734B2
Reaction notes
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