Dimedone → HCID 57670960, compound

HRID 1364348Notes

Reaction equation

HRID 1364348 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-d8a17ff115874667a0fabf711d604765
Source dataset
uspto-grants-2011_02
Patent number
US07888348B2

Reaction notes

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