Hydrochloric Acid → 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid

HRID 1051028Notes

Reaction equation

HRID 1051028 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=2)[O:22][CH2:23][C:24]([O:26]CC)=[O:25])(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O1CCCC1.Cl>O>[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[F:38])[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=2)[O:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90168788ethyl 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetate

Product 1

HCID 901689202-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetate 9a (170 mg, 0.31 mmol) and lithium hydroxide (71 mg, 3.0 mmol) were added to 20 mL of a mixed solvent of tetrahydrofuran and water (V/V=1:1) and then the reaction solution was stirred for 3 h. 1M of hydrochloric acid was added dropwise until the pH of the reaction solution was 5, and then it was extracted with ethyl acetate (30 mL×2). The organic phases were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain the title product 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetic acid 9b (160 mg, a yellow oil), which was used directly in the next step.

Workup

  1. extractionit was extracted with ethyl acetate (30 mL×2)
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-61d98d934ae947ab97f84cba11a2fbfe
Source dataset
uspto-grants-2016_07
Patent number
US09388133B2

Reaction notes

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