Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester → (+/-)-4,5-dihydro-4-ethoxy-(2-mercapto-1-oxopropyl)-1H-pyrrole-2-carboxylic acid
Reaction equation
C([O:5][C:6](=[O:15])[C@@H:7]1[CH2:11][CH:10]([O:12][CH2:13][CH3:14])[CH2:9][NH:8]1)(C)(C)C.C([O:18][CH:19]1CN[C@H:21](C(O)=O)[CH2:20]1)C.N1CCC[C@H]1C(O)=O.C(OC(=O)[C@@H]1CCCN1)(C)(C)C.C(CC(Cl)=[S:52])(=O)C.C(SCC(C)C(Cl)=O)(=O)C>>[CH2:13]([O:12][CH:10]1[CH2:9][N:8]([C:19](=[O:18])[CH:20]([SH:52])[CH3:21])[C:7]([C:6]([OH:5])=[O:15])=[CH:11]1)[CH3:14]Participants
7
Reactant 6
Product 1
Procedure
By substituting 4-ethoxy-L-proline tert-butyl ester [prepared from 4-ethoxy-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 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-ethoxy-(2-mercapto-1-oxopropyl)-1H-pyrrole-2-carboxylic acid is obtained.
Sources & evidence
- ORD record
- ord-e788f2940dae4330acc44199a54f2307
- Source dataset
- uspto-grants-1980_09
- Patent number
- US04221912
Reaction notes
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