Diisopropylethylamine → HCID 18713515, compound
Reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([N:16]2[CH2:20][C@@H:19]([CH:21]3[CH2:23][CH2:22]3)[C@H:18]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH2:17]2)=[O:15])[CH:7]=[CH:6]1.C(N([CH:44]([CH3:46])C)CC)(C)C.[C:47]([O-])([OH:49])=[O:48].[Na+]>>[CH2:44]([O:49][C:47]([NH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[C:14]([N:16]2[CH2:20][C@@H:19]([CH:21]3[CH2:23][CH2:22]3)[C@H:18]([CH2:24][N:25]3[CH2:30][CH2:29][CH:28]([C:31]4[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=4)[CH2:27][CH2:26]3)[CH2:17]2)=[O:15])[CH:7]=[CH:6]1)=[O:48])[CH3:46]Participants
4
Procedure
To a solution of 0.02 g (0.4 mmol) of 1-(N-(3-aminopropyl)-7-indolecarbonyl)-3-(R)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(S)-(cyclopropyl)pyrrolidine and 0.02 mL (0.12 mmol) of diisopropylethylamine in 2 mL of CH2C2 was added 0.007 mL (3 mmol) of ethylchlorofornate and the reaction mixture was stirred overnight at rt. To the reaction mixture was added 1 mL of sat'd NaHCO3 solution and the mixture was partitioned between EtOAc and water. The organic fractions were washed with sat'd NaCl solution, dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:3) to give 15 mg of the title compound. Mass Spectrum (EI) m/e 575 (M+1).
Workup
- customthe mixture was partitioned between EtOAc and water
- washThe organic fractions were washed with sat'd NaCl solution
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationthe filtrate was concentrated
- customThe residue was purified by chromatography (silica, acetone:hexanes, 1:3)
Sources & evidence
- ORD record
- ord-5bb570afa7db43e1b2329c41b1cbf6a7
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362201B1
Reaction notes
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