1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57173565, compound

HRID 703587Notes

Reaction equation

HRID 703587 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][C:24](O)=[O:25])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]1([CH3:36])[O:33][C:32](=[O:34])[CH2:31][C:30](=[O:35])[O:29]1.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@H:14]([O:16][S:17]([CH3:20])(=[O:19])=[O:18])[CH2:13][C@H:12]1[CH2:21][O:22][CH2:23][C:24]([CH:31]1[C:32](=[O:34])[O:33][C:28]([CH3:36])([CH3:27])[O:29][C:30]1=[O:35])=[O:25])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 54131619HCID 54131619, compound

Product 1

HCID 57173565HCID 57173565, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-benzyloxycarbonyl-2-carboxymethyloxymethyl-4-methanesulfonyloxypyrrolidine (79.4 g), 2,2-dimethyl-1,3-dioxane-4,6-dione (29.55 g) and 4-(dimethylamino)pyridine (25.05 g) in dichloromethane (635 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (39.3 g) at 5°-10° C. The solution was stirred at the same temperature for one hour and at ambient temperature for 18 hours. The mixture was washed with water (650 ml), 1N hydrochloric acid (650 ml), saturated aqueous sodium hydrogen carbonate (650 ml), and brine (650 ml) successively, dried over magnesium sulfate, and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (800 g) and eluted with a mixture of methanol and dichloromethane (2:98 V/V) to give (2S,4R)-1-benzyloxycarbonyl-2-[2-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)-2-oxoethyl]oxymethyl-4-methanesulfonyloxypyrrolidine (80.98 g).

Workup

  1. washThe mixture was washed with water (650 ml), 1N hydrochloric acid (650 ml), saturated aqueous sodium hydrogen carbonate (650 ml), and brine (650 ml) successively
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a syrup
  5. washeluted with a mixture of methanol and dichloromethane (2:98 V/V)

Sources & evidence

ORD record
ord-f389922703e64c6088d7377ac9ec1a92
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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