Dimedone → HCID 126504116, compound

HRID 626438Notes

Reaction equation

HRID 626438 reaction equation
C(OC([NH:7][C@H:8]([C:15]([NH:17][C:18]1[CH:19]=[C:20]([C@@H:25]([CH3:34])[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:21]=[CH:22][C:23]=1[Cl:24])=[O:16])[CH:9]([C:11]([F:14])([F:13])[F:12])[CH3:10])=O)C=C.CC1(C)CC(=O)CC(=O)C1>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.C1COCC1>[Cl:24][C:23]1[CH:22]=[CH:21][C:20]([C@@H:25]([CH3:34])[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])=[CH:19][C:18]=1[NH:17][C:15](=[O:16])[C@H:8]([CH:9]([C:11]([F:14])([F:13])[F:12])[CH3:10])[NH2:7]

Participants

5

Reactant 2

HCID 31358DimedoneHCID 126504110HCID 126504110, compound

Product 1

HCID 126504116HCID 126504116, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.39 g (2.74 mmol) of tert-butyl (3S)-3-[3-({N-[(allyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]butanoate (Example 41A, mixture of 4 isomers) and 3.08 g (21.9 mmol) of dimedone were initially charged in 9.4 ml of abs. THF. At RT, the solution was deoxygenated by passing through argon for 30 min Subsequently 63.4 mg (0.055 mmol) of tetrakis(triphenylphosphine)palladium(0) were added and the mixture was stirred at RT overnight. After dilution with ethyl acetate, the mixture was washed twice with sat. sodium bicarbonate solution and once with sat. sodium chloride solution. The organic phase was dried over magnesium sulphate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→20:1) and separated. This gave 950 mg of the target compound as diastereomer mixture 1 (81.9% of theory).

Workup

  1. customAt RT, the solution was deoxygenated
  2. washAfter dilution with ethyl acetate, the mixture was washed twice with sat. sodium bicarbonate solution and once with sat. sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 40:1→20:1)
  6. customseparated

Sources & evidence

ORD record
ord-dec57a348bed45e5a1a080dbc7fec362
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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