Hydrochloric Acid → (E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester

HRID 1802781Notes

Reaction equation

HRID 1802781 reaction equation
[CH3:1][O:2][C:3](=[O:36])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:35])=[N:21][N:22](S(C3C=CC(C)=CC=3)(=O)=O)[C:23]=2[CH3:24])=[CH:8][CH:7]=1.C[O-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:36])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][C:9]([C@@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH2:17][CH2:18][C:19]2[C:20]([CH3:35])=[N:21][NH:22][C:23]=2[CH3:24])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 57899210(E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester

Product 1

HCID 57899243(E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (E)-3-[4-((S)-1-{2-[3,5-dimethyl-1-(toluene-4-sulfonyl)-1H-pyrazol-4-yl]-ethyl}-pyrrolidin-2-yl)-phenyl]-acrylic acid methyl ester (200 mg, 0.394 mmol) in methanol (10 mL) was added sodium methoxide in methanol (25 wt %, 1.0 mL). The mixture was subjected to microwave irradiation for 10 minutes, neutralized with 1 N HCl, and concentrated in vacuo. The remaining aqueous layer was extracted with ethyl acetate and dichloromethane, and the organic extracts were combined, dried over magnesium sulfate and concentrated in vacuo to give (E)-3-(4-{(S)-1-[2-(3,5-dimethyl-1H-pyrazol-4-yl)-ethyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester as a yellow crude oil (126 mg) that was directly used in the next step.

Workup

  1. customirradiation for 10 minutes
  2. concentrationconcentrated in vacuo
  3. extractionThe remaining aqueous layer was extracted with ethyl acetate and dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-98c8bebf4d294716b2182fa765ce47d9
Source dataset
uspto-grants-2013_01
Patent number
US08349883B2

Reaction notes

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