Dimedone → HCID 118122135, compound

HRID 626439Notes

Reaction equation

HRID 626439 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])[C@H: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]([C@H:9]([C:11]([F:14])([F:13])[F:12])[CH3:10])[NH2:7]

Participants

5

Reactant 2

HCID 31358DimedoneHCID 131735220HCID 131735220, compound

Product 1

HCID 118122135HCID 118122135, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.30 g (2.56 mmol) of tert-butyl (3S)-3-[3-({(3R)—N-[(allyloxy)carbonyl]-4,4,4-trifluorovalyl}amino)-4-chlorophenyl]butanoate (Example 42A, diastereomer mixture) and 2.88 g (20.5 mmol) of dimedone were initially charged in 8.7 ml of abs. THF. At RT, the solution was deoxygenated by passing through argon for 30 min. Subsequently 59.3 mg (0.051 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 10:1) and separated. This gave 591 mg of the target compound (54.5% 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 10:1)
  6. customseparated

Sources & evidence

ORD record
ord-edc1bcf1688542408c05d941ec477599
Source dataset
uspto-grants-2016_04
Patent number
US09309198B2

Reaction notes

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