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

HRID 1189557Notes

Reaction equation

HRID 1189557 reaction equation
[C:1]([C:3]1[C:7]([CH3:8])=[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])[N:5]([CH2:24][C:25]([O:27]CC)=[O:26])[C:4]=1[CH3:30])#[N:2].O.[OH-].[Li+].Cl>C1COCC1.CO.ClCCl>[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[S:16]([N:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)(=[O:18])=[O:17])[N:5]([CH2:24][C:25]([OH:27])=[O:26])[C:4]=1[CH3:30])#[N:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58310969ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate

Product 1

HCID 583109612-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acidYield 108.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (286.9 mg, 0.668 mmol) in THF (8.0 ml), MeOH (2.7 ml), and water (2.7 ml) at 0° C., was added lithium hydroxide (32.0 mg, 1.336 mmol). The mixture was stirred for 1 hour. To this mixture, was then added HCl (1336 μl, 1.336 mmol) and the resulting mixture 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-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (290.0 mg, 0.722 mmol, 108% yield) as a solid. 1H NMR (CDCl3/400 MHz) δ (ppm) 9.52 (bs, 1H), 7.87-7.82 (m, 1H), 7.42-7.35 (m, 1H), 7.34-7.28 (m, 1H), 6.92-6.86 (m, 1H), 4.33 (s, 2H), 4.25 (s, 2H), 3.40-3.28 (m, 4H), 2.25 (s, 3H), 2.10 (s, 3H), 1.97-1.91 (m, 4H). MS m/z: 402.3 (M+1).

Workup

  1. washwashed with water (20 ml×3)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c948dc1114a045ff8c3da5158be03fc6
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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