Hydrochloric Acid → (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester

HRID 1058427Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058427
CN(C)C(N(C)C)=N.[CH3:9][O:10][C:11](=[O:40])[CH:12](P(OC)(OC)=O)[NH:13][C:14](=[O:33])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:17][C:16]=1Cl.[Br:41][C:42]1[CH:49]=[CH:48][C:45]([CH:46]=O)=[CH:44][CH:43]=1.[ClH:50]>O1CCCC1.O1CCOCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[NH:13][C:14](=[O:33])[C:15]1[CH:16]=[CH:17][C:18]([C:21]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([OH:31])[CH:26]=2)=[O:22])=[CH:19][C:20]=1[Cl:50])=[CH:46]/[C:45]1[CH:48]=[CH:49][C:42]([Br:41])=[CH:43][CH:44]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 664601,1,3,3-TetramethylguanidineHCID 707414-BromobenzaldehydeHCID 23560750HCID 23560750, Verbindung

Produkt 1

HCID 59038409(Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl esterAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

1,1,3,3-Tetramethylguanidine (0.047 g, 0.41 mmol) was added to a solution of rac.-N-[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 141; 0.10 g, 0.21 mmol) and 4-bromobenzaldehyde (0.076 g, 0.412 mmol) in tetrahydrofuran (1.5 mL). Dioxane (1.5 mL) was added to bring everything into solution and the reaction mixture was stirred at room temperature for 15 h. The solution was then poured into 1N hydrochloric acid solution and the aqueous phase was extracted with ethyl acetate. The organic layer was concentrated in vacuo and the residual material was chromatographed over silica gel (45% ethyl acetate/hexanes) to give (Z)-3-(4-bromophenyl)-2-[[2-chloro-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]propenoic acid methyl ester (69 mg, 62% yield).

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate
  2. concentrationThe organic layer was concentrated in vacuo
  3. customthe residual material was chromatographed over silica gel (45% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-8fa00c8d5dd44fd08da5f7d45474c37c
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515124B2

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