2-Naphthalenecarboxaldehyde → (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl ester

HRID 1058416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058416
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]=1[Br:32].[CH:41]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=[CH:43][C:42]=1[CH:51]=O.C(OCC)(=O)C>O1CCCC1>[CH3:9][O:10][C:11](=[O:40])/[C:12](/[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]=1[Br:32])=[CH:51]/[C:42]1[CH:43]=[CH:44][C:45]2[C:50](=[CH:49][CH:48]=[CH:47][CH:46]=2)[CH:41]=1

Komponenten

6

Edukt 4

HCID 62012-NaphthalenecarboxaldehydeHCID 8857Ethyl AcetateHCID 664601,1,3,3-TetramethylguanidineHCID 23560709Rac.-n-[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester

Produkt 1

HCID 59038424(Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl esterAusbeute 78,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

1,1,3,3-Tetramethylguanidine (50.5 μL, 0.40 mmol) was added to a solution of rac.-N-[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]-2-(dimethoxyphosphinyl)glycine methyl ester (Example 130; 106.4 mg, 0.20 mmol) in tetrahydrofuran (1 mL) at −20° C. After 5 min, a solution of naphthalene-2-carboxaldehyde (31.4 mg, 0.20 mmol) in tetrahydrofuran (0.5 mL) was added. The solution was stirred at −20° C. for 1 h and then was stirred at room temperature for 4 h. Ethyl acetate (15 mL) was added and the solution was washed with 1N hydrochloric acid solution (10 mL) and brine (10 mL). The dried (MgSO4) organic phase was filtered, evaporated and the resulting residue was triturated with petroleum ether to furnish (Z)-2-[[2-bromo-4-[[(3-hydroxybenzyl)amino]carbonyl]benzoyl]amino]-3-(naphthalen-2-yl)propenoic acid methyl ester (88 mg, 78% yield) as a yellow solid.

Aufarbeitung

  1. stirringwas stirred at room temperature for 4 h
  2. washthe solution was washed with 1N hydrochloric acid solution (10 mL) and brine (10 mL)
  3. dry with materialThe dried (MgSO4) organic phase
  4. filtrationwas filtered
  5. customevaporated
  6. customthe resulting residue was triturated with petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-0cad13dda78343c9a5ec91b267cb464c
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06515124B2

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