Sodium Hydroxide → 4-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid

HRID 1755101Notes

Reaction equation

HRID 1755101 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:44])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][S:14]([N:17]2[CH2:42][CH2:41][C:20]3([N:24]=[C:23]([C:25]4[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[C:27]([O:35][CH2:36][CH2:37][CH:38]=[CH2:39])[CH:26]=4)[NH:22][C:21]3=[O:40])[CH2:19][CH2:18]2)(=[O:16])=[O:15])=[C:8]([CH3:43])[CH:7]=1>CO>[CH2:36]([O:35][C:27]1[CH:26]=[C:25]([C:23]2[NH:22][C:21](=[O:40])[C:20]3([CH2:41][CH2:42][N:17]([S:14]([CH2:13][CH2:12][C:9]4[CH:10]=[CH:11][C:6]([C:5]([OH:44])=[O:4])=[CH:7][C:8]=4[CH3:43])(=[O:16])=[O:15])[CH2:18][CH2:19]3)[N:24]=2)[CH:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=1)[CH2:37][CH:38]=[CH2:39]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 668187074-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester

Product 1

HCID 668170254-{2-[2-(3-But-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acidYield 86.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5 N aqueous sodium hydroxide solution (6.6 ml, 33 mmol) was added to a solution of 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid methyl ester (2.10 g) in methanol (22 ml), and the mixture was stirred at room temperature for two hours. The reaction solution was cooled and then quenched with 2 N hydrochloric acid (25 ml), followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to give 4-{2-[2-(3-but-3-enyloxy-5-trifluoromethyl-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-3-methyl-benzoic acid (1.78 g).

Workup

  1. temperatureThe reaction solution was cooled
  2. customquenched with 2 N hydrochloric acid (25 ml)
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-769fb9a4cc634419a865e037b0de3d7c
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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