Bromine → 1-[3-(Benzoylthio)-3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline

HRID 66537Notes

Reaction equation

HRID 66537 reaction equation
BrBr.Br[CH:4]([C:16]([C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][CH:22]=1)=[O:17])[CH2:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7].[C:24]([O-:32])(=[S:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[Na+]>C(O)(=O)C>[C:24]([S:31][CH:4]([C:16]([C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][CH:22]=1)=[O:17])[CH2:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])=[O:7])(=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 23688990Benzenecarbothioic acid, sodium salt (1:1)HCID 867380941-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline

Product 1

HCID 543346981-[3-(Benzoylthio)-3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

As for Example 1, the preceding compound is coupled to L-proline to give 1-[3-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline. The preceding compound (0.01 mole) is brominated with bromine (0.011 mole) in acetic acid and the resulting 1-[3-bromo-(1-methyl-2-pyrrolylcarbonyl)propionyl]-L-proline (0.01 mole) is reacted with sodium thiobenzoate as for Example 21 to give the product of the Example as a glass.

Workup

  1. customto give the product of the Example as a glass

Sources & evidence

ORD record
ord-3fee6a6ba4e04c6ea29d7b7d83e7abbb
Source dataset
uspto-grants-1982_08
Patent number
US04342691

Reaction notes

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