Sodium Hydroxide → (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid

HRID 1058442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058442
[OH-].[Na+].C[O:4][C:5](=[O:36])/[C:6](/[NH:15][C:16](=[O:35])[C:17]1[CH:22]=[CH:21][C:20]([C:23](=[O:33])[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:19][C:18]=1[Cl:34])=[CH:7]/[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14]>CO.O1CCCC1>[Cl:34][C:18]1[CH:19]=[C:20]([C:23](=[O:33])[CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[CH:21]=[CH:22][C:17]=1[C:16]([NH:15]/[C:6](=[CH:7]\[C:8]1[S:12][C:11]([CH3:13])=[N:10][C:9]=1[CH3:14])/[C:5]([OH:36])=[O:4])=[O:35]

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 59038456(Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester

Produkt 1

HCID 59038360(Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

An aqueous 1N solution of sodium hydroxide (0.6 mL, 0.6 mmol) was added to a solution of (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid methyl ester (Example 227; 95 mg, 0.19 mmol) in methanol/tetrahydrofuran (1:1; 2.4 mL). The solution was stirred at room temperature for 6 h and the solvent was evaporated. Water (5 mL) was added and the mixture was extracted with diethyl ether. The organic extract was discarded and the aqueous layer was acidified with 1N hydrochloric acid solution (0.6 mL) and stirred for 30 min at room temperature. The resulting precipitate was filtered off, washed with water, dried and crystallized from tetrahydrofuran/methanol/water to furnish (Z)-2-[[2-chloro-4-[3-(3-hydroxyphenyl)-1-oxopropan-1-yl]benzoyl]amino]-3-(2,4-dimethylthiazol-5-yl)propenoic acid (65 mg, 71% yield) as a colorless solid.

Aufarbeitung

  1. customthe solvent was evaporated
  2. additionWater (5 mL) was added
  3. extractionthe mixture was extracted with diethyl ether
  4. extractionThe organic extract
  5. stirringstirred for 30 min at room temperature
  6. filtrationThe resulting precipitate was filtered off
  7. washwashed with water
  8. customdried
  9. customcrystallized from tetrahydrofuran/methanol/water

Quellen und Nachweise

ORD-Eintrag
ord-f4dcf3a20ad54eaa984f82a5d860b79d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515124B2

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