2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 58857980, compound

HRID 1162366Notes

Reaction equation

HRID 1162366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:37])[NH:10][CH:11]([C:33]([CH3:36])([CH3:35])[CH3:34])[C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]3[CH:25]=[CH:24][S:23]/[C:22]/3=[N:26]\C(=O)OCC=C)[CH2:16][CH2:15]2)=[O:13])=[CH:4][CH:3]=1.CC1(C)OC(=O)CC(=O)O1>C1COCC1.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>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:10][C@@H:11]([C:12]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][N:21]3[CH:25]=[CH:24][S:23][C:22]3=[NH:26])[CH2:16][CH2:15]2)=[O:13])[C:33]([CH3:35])([CH3:34])[CH3:36])=[O:37])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 87529120HCID 87529120, compound

Product 1

HCID 58857980HCID 58857980, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Allyl(2Z)-3-(1-(2-(N′-(4-chlorophenyl)ureido)-3,3-dimethylbutyroyl)-4-piperidinyl)methyl-1,3-thiazol-2(3H)-ylidenecarbamate (0.33 g) obtained in Example 139c) and meldrum's acid (0.13 g) were dissolved in THF (10 ml). The solution was deaerated and substituted with argon. Tetrakis(triphenylphosphine)palladium (0.07 g) was added thereto, and mixed under argon atmosphere for 12 hours. The precipitated insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified with silica gel column to obtain the title compound as a pale yellow solid (0.14 g, 51%).

Workup

  1. additionmixed under argon atmosphere for 12 hours
  2. filtrationThe precipitated insolubles were filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-ee6b8107025b4862860739c3f0d9ad17
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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