Diisopropylethylamine → 1-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)pentane

HRID 1008291Notes

Reaction equation

HRID 1008291 reaction equation
[CH3:1][O:2][C:3]1([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:7][C:6](=[O:8])[CH:5]([CH:9]([CH2:13][CH2:14][CH2:15][CH3:16])[C:10](O)=[O:11])[O:4]1.[C:23]([O:27][C:28](=[O:34])[C@@H:29]1[CH2:33][CH2:32][CH2:31][NH:30]1)([CH3:26])([CH3:25])[CH3:24].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>[CH3:1][O:2][C:3]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[O:7][C:6](=[O:8])[CH:5]([CH:9]([C:10]([N:30]2[CH2:31][CH2:32][CH2:33][C@H:29]2[C:28]([O:27][C:23]([CH3:26])([CH3:24])[CH3:25])=[O:34])=[O:11])[CH2:13][CH2:14][CH2:15][CH3:16])[O:4]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 226668912-(2-Methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid

Product 1

HCID 865857091-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)pentaneYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 2-(2-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)hexanoic acid I-1 (10 mmol; prepared as described in Method I, 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-methoxy-2-phenyl-4-oxo-1,3-dioxolan-5-yl)-1-(2-(S)-tert-butoxycarbonylpyrrolidin-1-yl-carbonyl)pentane 1-2 (5 mmol, 50%).

Workup

  1. washwashed with water, sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationThe filtrate was concentrated
  4. custompurified on silica gel (Merck 60; ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a688bdf22bb0415f9f334dbd7991dd4f
Source dataset
uspto-grants-2004_09
Patent number
US06797820B2

Reaction notes

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