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Hydrochloric Acid → 5-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid

HRID 2235327
Notes
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Reaction equation

HRID 2235327 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[S:8][C:9]([C:12]2[CH:17]=[C:16]([Cl:18])[C:15]([CH2:19][CH:20]3[CH2:24][CH2:23][N:22]([CH:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)[C:21]3=[O:31])=[C:14]([Cl:32])[CH:13]=2)=[CH:10][CH:11]=1)=[O:6].CCOC(C)=O.Cl>O1CCOCC1>[Cl:32][C:14]1[CH:13]=[C:12]([C:9]2[S:8][C:7]([C:5]([OH:6])=[O:4])=[CH:11][CH:10]=2)[CH:17]=[C:16]([Cl:18])[C:15]=1[CH2:19][CH:20]1[CH2:24][CH2:23][N:22]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:21]1=[O:31]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 592993875-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 592994935-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid

Reagents, catalysts & solvents

1
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

Add 1.0 mL of LiOH (2.0 N aq.) to a solution of 5-[3,5-Dichloro-4-(1-cyclohexyl-2-oxo-pyrrolidin-3-ylmethyl)-phenyl]-thiophene-2-carboxylic acid methyl ester (85 mg, 0.182 mmol) in 3.0 mL of dioxane and heat to 50° C. After 3 hours, a TLC shows the reaction to be complete. Dilute the reaction with DCM /H2O (50/50), acidify with 1.0N HCl, extract with ethyl acetate, and dry the combined organic layers with sodium sulfate. Filter off the sodium sulfate and concentrate to give the title compound. LC/MS (API) m/z: 452.0 (M+1).

Workup

  1. customthe reaction
  2. additionDilute
  3. extractionextract with ethyl acetate
  4. dry with materialdry the combined organic layers with sodium sulfate
  5. filtrationFilter off the sodium sulfate
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-5281614b7388400c99098fc838bf2d33
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713979B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes