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Hydrochloric Acid → 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

HRID 1189556
Notes
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Reaction equation

HRID 1189556 reaction equation
[C:1]([C:3]1[N:4]([CH2:25][C:26]([O:28]CC)=[O:27])[C:5]([CH3:24])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:18])=[O:17])[C:7]=1[CH3:8])#[N:2].O.[OH-].[Li+].Cl>C1COCC1.CO>[C:1]([C:3]1[N:4]([CH2:25][C:26]([OH:28])=[O:27])[C:5]([CH3:24])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)(=[O:17])=[O:18])[C:7]=1[CH3:8])#[N:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 53245904ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Product 1

HCID 532460252-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (40.0 mg, 0.093 mmol) in THF (1.1 ml), MeOH (372 μl), and Water (372 μl) at 0° C., was added lithium hydroxide (5.2 mg, 0.217 mmol). The mixture was stirred for 1 hour. This mixture was left standing over the course of 2 days at room temperature. To this mixture, was added HCl (214 μl, 0.214 mmol), then, the mixture was concentrated under vacuum, diluted in dichloromethane (50 ml) and washed with water (20 ml×3). The organic layer was dried, filtered, and evaporated to give 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid as a solid. 1H NMR (CDCl3/400 MHz) δ (ppm) 7.95-7.90 (m, 1H), 7.43-7.37 (m, 1H), 7.34-7.28 (m, 1H), 6.92-6.86 (m, 1H), 4.77 (s, 2H), 4.19 (s, 2H), 3.44-3.33 (m, 4H), 2.07 (s, 3H), 2.02 (s, 3H), 1.98-1.93 (m, 4H). MS m/z: 402.3 (M+1).

Workup

  1. waitThis mixture was left
  2. customstanding over the course of 2 days at room temperature
  3. concentrationthe mixture was concentrated under vacuum
  4. additiondiluted in dichloromethane (50 ml)
  5. washwashed with water (20 ml×3)
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-74cb4b281ae045c09fffb6c4a57daf7c
Source dataset
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08674115B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes