Dimedone → HCID 57670960, compound

HRID 554795Notes

Reaction equation

HRID 554795 reaction equation
[CH2:1]([CH:8]([C:24]([NH:26][S:27]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)(=[O:29])=[O:28])=[O:25])[CH2:9][N:10]([CH2:16][C:17]([O:19]C(C)(C)C)=[O:18])[C:11](=[O:15])[CH2:12]C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1(C)CC(=O)CC(=O)C1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([CH:8]1[CH2:9][N:10]([CH2:16][C:17]([OH:19])=[O:18])[C:11](=[O:15])[CH2:12][N:26]([S:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)(=[O:29])=[O:28])[C:24]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 31358DimedoneHCID 86629969HCID 86629969, compound

Product 1

HCID 57670960HCID 57670960, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the tert-butyl [(2-benzyl-3-{[(4-chlorophenyl)sulfonyl]amino}-3-oxopropyl)(3-butenoyl)amino]acetate (505 mg), synthesized by using, instead of the starting material compound of Reference Example 117, that is, the compound S6, the compound S175 for the similar procedure as in Reference Example 117, in tetrahydrofuran (10 ml) solution, tetrakis(triphenylphosphine)palladium (0) (104 mg) and dimedone (1 g) were added and the mixture was stirred at room temperature for 1 hour. The reaction solution was concentrated and suspended in methanol-diethylether, and the precipitate was collected by filtration. The collected precipitate was used for the similar procedure was followed as in Reference Example 124, Example 1, and Example 251 to obtain the title compound.

Workup

  1. concentrationThe reaction solution was concentrated
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-a644eeb4caaf4c1caf9f5bd37312dc98
Source dataset
uspto-grants-2011_11
Patent number
US08049006B2

Reaction notes

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