Diisopropylethylamine → 1-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)pentane
Reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][C:5](=[O:7])[CH:4]([CH:8]([CH2:12][CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=O)[O:3]1.[C:17]([O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1)([CH3:20])([CH3:19])[CH3:18].CCN(C(C)C)C(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[CH3:16][C:2]1([CH3:1])[O:6][C:5](=[O:7])[CH:4]([CH:8]([C:9]([N:24]2[CH2:25][CH2:26][CH2:27][C@H:23]2[C:22]([O:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:28])=[O:11])[CH2:12][CH2:13][CH2:14][CH3:15])[O:3]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 2-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid G-1 (10 mmol; prepared as described in Method F, above) in DMF (50 mL) was added proline O-t-butyl ester (10 mmol), DIEA (25 mmol) and PyBOP (10 mmol) and the solution stirred for 8 h. The reaction was diluted with ethyl acetate and washed with water, sodium bicarbonate, brine, and then dried (Na2SO4). The filtrate was concentrated and then purified on silica gel (Merck 60; ethyl acetate/hexane) to afford 1-(2,2-dimethyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-ylcarbonyl)pentane G-2 (5 mmol, 50%).
Workup
- washwashed with water, sodium bicarbonate, brine
- dry with materialdried (Na2SO4)
- concentrationThe filtrate was concentrated
- custompurified on silica gel (Merck 60; ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-e81ce47e6d7241eb9a0bd444b123bcfd
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797820B2
Reaction notes
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