Water → HCID 67361977, compound

HRID 1183173Notes

Reaction equation

HRID 1183173 reaction equation
Cl.[NH2:2][C@H:3]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.O.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([C:39](Cl)=[O:40])=[N:33]1>CC1CCCO1>[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[C:36]([O:37][CH3:38])=[CH:35][C:34]([C:39]([NH:2][C@H:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:40])=[N:33]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 67362509HCID 67362509, compoundHCID 86676960HCID 86676960, compound2×

Product 1

HCID 67361977HCID 67361977, compound

Reagents, catalysts & solvents 1

HCID 73012-MethyltetrahydrofuranSolvent

Procedure

A solution of ethyl (S)-3-amino-3-(2-methyl-phenyl)-propionate hydrochloride (42.4 g, 174 mmol) in 2-methyltetrahydrofuran (200 ml) was added to the suspension of 1-(2-fluoro-phenyl)-5-methoxy-1H-pyrazole-3-carbonyl chloride in ca. 200 ml of 2-methyltetrahydrofuran obtained in step 1. Triethylamine (33.5 g, 331 mmol) was added dropwise under ice cooling. After the complete addition of the triethylamine the conversion was complete and water was added. The phases were separated and the organic phase was washed with water and evaporated. The residue was dissolved in 2-methyltetrahydrofuran (500 ml) and washed with 1 M hydrochloric acid. The organic phase was dried and the solvent was removed under reduced pressure to give 70.4 g (99% over two step) of the title compound as a light brown oil.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with water
  3. customevaporated
  4. dissolutionThe residue was dissolved in 2-methyltetrahydrofuran (500 ml)
  5. washwashed with 1 M hydrochloric acid
  6. customThe organic phase was dried
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0c93dd7e9f494f8ab9deb90b872aa7f0
Source dataset
uspto-grants-2014_03
Patent number
US08664257B2

Reaction notes

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