Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester → 4,5-dihydro-4-chloro-1-(2-mercaptoacetyl)-1H-pyrrole-2-carboxylic acid

HRID 27608

Reaktionsgleichung

Reaktionsgleichung von HRID 27608
C([O:5][C:6](=[O:13])[C@@H:7]1[CH2:11][CH:10]([Cl:12])[CH2:9][NH:8]1)(C)(C)C.ClC1CN[C@H:17]([C:20]([OH:22])=O)C1.N1CCC[C@H]1C(O)=O.C(OC(=O)[C@@H]1CCCN1)(C)(C)C.C(CC(Cl)=[S:48])(=O)C.C(SCC(C)C(Cl)=O)(=O)C>>[Cl:12][CH:10]1[CH2:9][N:8]([C:20](=[O:22])[CH2:17][SH:48])[C:7]([C:6]([OH:5])=[O:13])=[CH:11]1

Komponenten

7

Edukt 6

HCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 145742L-ProlineHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 228106424-ChloroprolineHCID 23301560AcetylthioacetylchlorideHCID 571178734-chloro-L-proline tertbutyl ester

Produkt 1

HCID 233431964,5-dihydro-4-chloro-1-(2-mercaptoacetyl)-1H-pyrrole-2-carboxylic acid

Versuchsvorschrift

By substituting 4-chloro-L-proline tert-butyl ester [prepared from 4-chloro-L-proline by the procedure described in J. Am. Chem. Soc., 82, 3359 (1960) for L-proline] for the L-proline tert-butyl ester and 2-acetylthioacetyl chloride for the 3-acetylthio-2-methylpropanoyl chloride in the procedure of Example 1 and then submitting the product to the procedure of Example 2, 4,5-dihydro-4-chloro-1-(2-mercaptoacetyl)-1H-pyrrole-2-carboxylic acid is obtained.

Quellen und Nachweise

ORD-Eintrag
ord-8a895aa894ce4bd9bc2e173e11add461
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04221912

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