Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester → (+/-)-4,5-dihydro-1-[3-[(2-furanylcarbonyl)thio]-2-methyl-1-oxopropyl]-1H-pyrrole-2-carboxylic acid

HRID 1856084Notes

Reaction equation

HRID 1856084 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([S:8][CH2:9][CH:10]([CH3:14])[C:11](Cl)=[O:12])=[O:7].C(SCC(C)C(Cl)=O)(=O)C.C(SCC(C)C([N:38]1[CH2:42][CH2:41][CH:40]=[C:39]1[C:43]([OH:45])=[O:44])=O)(=O)C1C=CC=CC=1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([S:8][CH2:9][CH:10]([CH3:14])[C:11]([N:38]1[CH2:42][CH2:41][CH:40]=[C:39]1[C:43]([OH:45])=[O:44])=[O:12])=[O:7]

Participants

4

Reactant 3

HCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) esterHCID 23347609(+/-)-1-[3-(benzoylthio)-2-methyl-1-oxopropyl]-4,5-dihydro-1H-pyrrole-2-carboxylic acidHCID 233476193-[(2-Furanylcarbonyl)thio]-2-methylpropanoyl chloride

Product 1

HCID 23347616(+/-)-4,5-dihydro-1-[3-[(2-furanylcarbonyl)thio]-2-methyl-1-oxopropyl]-1H-pyrrole-2-carboxylic acid

Procedure

Following the procedure of Example 1 but substituting an equivalent amount of 3-[(2-furanylcarbonyl)thio]-2-methylpropanoyl chloride for the 3-acetylthio-2-methylpropanoyl chloride in part (b) and subjecting the product to the procedure of Example 1(c), one obtains (±)-4,5-dihydro-1-[3-[(2-furanylcarbonyl)thio]-2-methyl-1-oxopropyl]-1H-pyrrole-2-carboxylic acid.

Sources & evidence

ORD record
ord-8af9bc59d3454d84bf876a5c0cbcf7a4
Source dataset
uspto-grants-1980_08
Patent number
US04217458

Reaction notes

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