Hydrochloric Acid → [3-[[Butyl[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]amino]methyl]phenyl]acetic acid

HRID 420589Notes

Reaction equation

HRID 420589 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][N:12]([CH2:28][CH2:29][CH2:30][CH3:31])[CH:13]2[CH2:17][CH2:16][N:15]([C:18]3[S:19][C:20]4[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:21]=4[N:22]=3)[CH2:14]2)[CH:6]=1.[OH-].[Na+].O1CCCC1.Cl>CO>[CH2:28]([N:12]([CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=1)[CH:13]1[CH2:17][CH2:16][N:15]([C:18]2[S:19][C:20]3[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:21]=3[N:22]=2)[CH2:14]1)[CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57966119[3-[[Butyl[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]amino]methyl]phenyl]acetic acid methyl ester

Product 1

HCID 57966534[3-[[Butyl[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]amino]methyl]phenyl]acetic acidYield 69.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of [3-[[butyl[1-(6-chlorobenzothiazole-2-yl)pyrrolidine-3-yl]amino]methyl]phenyl]acetic acid methyl ester (28 mg), 2N sodium hydroxide (0.15 mL), tetrahydrofuran (1 mL) and methanol (0.5 mL) was stirred at room temperature for 1 hour. The mixture was neutralized with 2N hydrochloric acid and concentrated under reduced pressure. The solution was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate to give the title compound (19 mg). Yield: 68%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulphate

Sources & evidence

ORD record
ord-fa7f4b4ece0d4e23bfb4616a7c887599
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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