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 1755101Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755101
[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]

Komponenten

4

Edukt 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

Produkt 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 acidAusbeute 86,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-769fb9a4cc634419a865e037b0de3d7c
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09169254B2

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