Nitroethane → (S)-4,5-Dihydro-2-(2-hydroxy-4-carboxyphenyl)-4-thiazolecarboxylic acid

HRID 983490

Reaktionsgleichung

Reaktionsgleichung von HRID 983490
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12])=O.C(C1C=CC(C(O)=O)=CC=1O)#N.[N+](CC)([O-])=O.[NH2:30][C@@H:31]([C:34]([OH:36])=[O:35])[CH2:32][SH:33]>C([O-])(=O)C.[Na+].C(O)(=O)C>[OH:12][C:4]1[CH:5]=[C:6]([C:7]([OH:9])=[O:8])[CH:10]=[CH:11][C:3]=1[C:1]1[S:33][CH2:32][C@H:31]([C:34]([OH:36])=[O:35])[N:30]=1

Komponenten

7

Edukt 4

HCID 6587NitroethaneHCID 92851D-CysteineHCID 3175084-Formyl-3-hydroxybenzoic acidHCID 105112024-Cyano-3-hydroxybenzoic acid

Produkt 1

HCID 135433801(S)-4,5-Dihydro-2-(2-hydroxy-4-carboxyphenyl)-4-thiazolecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 517045Sodium AcetateLösungsmittel

Versuchsvorschrift

The key step of the synthesis of (S)-4,5-dihydro-2-(2-hydroxy-3-methoxyphenyl)-4-thiazolecarboxylic acid (6) was cyclocondensation of D-cysteine with 2-hydroxy-3-methoxybenzonitrile. The cyano intermediate was obtained from o-vanillin by treatment with nitroethane in sodium acetate and acetic acid. (S)-4,5-Dihydro-2-(2-hydroxy-4-carboxyphenyl)-4-thiazolecarboxylic acid (7) was synthesized by a similar reaction sequence. 4-Formyl-3-hydroxybenzoic acid was converted to 4-cyano-3-hydroxybenzoic acid using nitroethane in sodium acetate and acetic acid; cyclization with D-cysteine completed the synthesis of dicarboxylic acid chelator 7.

Quellen und Nachweise

ORD-Eintrag
ord-cbcddaa4e9bd4285aed1468f28959065
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06864270B2

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