Dicyclohexylcarbodiimide → HCID 15117292, compound

HRID 1029657Notes

Reaction equation

HRID 1029657 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][C@H:8]1[C:13]([OH:15])=O)=[O:6])[CH:2]=[CH2:3].[CH3:16][C:17]1([CH3:25])[O:22][C:21](=[O:23])[CH2:20][C:19](=[O:24])[O:18]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][C@H:8]1[C:13]([CH:20]1[C:21](=[O:23])[O:22][C:17]([CH3:25])([CH3:16])[O:18][C:19]1=[O:24])=[O:15])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 151172913,4-Morpholinedicarboxylic acid, 4-(2-propenyl) ester, (S)-

Product 1

HCID 15117292HCID 15117292, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of (3S)-4-allyloxycarbonylmorpholine-3-carboxylic acid (5.20 g) and 2,2-dimethyl-1,3-dioxane-4,6-dione (3.5 g) in dichloromethane (50 ml) were added dicyclohexylcarbodiimide (5.00 g) and 4-dimethylaminopyridine (2.96 g), in turn, under ice-cooling. The mixture was stirred under ice-cooling for 2 hours and at ambient temperature for 18 hours. Insoluble material was filtered off. The filtrate was washed with 1N hydrochloric acid (50 ml×2) and, next, brine (50 ml), dried over magnesium sulfate, and concentrated under reduced pressure to give 5-[(3S)-4-allyloxycarbonylmorpholin-3-yl]carbonyl-2,2-dimethyl-1,3-dioxane-4,6-dione (8.31 g) as a syrup.

Workup

  1. temperaturein turn, under ice-cooling
  2. filtrationInsoluble material was filtered off
  3. washThe filtrate was washed with 1N hydrochloric acid (50 ml×2)
  4. dry with materialnext, brine (50 ml), dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d57d7d1d8ba34b6799925f60be3d86c3
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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