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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 549408
Notes
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Reaction equation

HRID 549408 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 887
Methanol
Solvent
2×

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-a7ef015805604571819756ed10a1e17b
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07943652B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes