Triethylamine → (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)octanamide

HRID 266365Notes

Reaction equation

HRID 266365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:26][CH:25]=1.C(N(CC)CC)C.[I-].C[N+]1C=CC=CC=1Cl>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:13]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:28][CH:29]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 19032932(RS)-2-(4-chlorobenzenesulfonylamino)octanoic acidHCID 24192282Ethyl (4-aminophenyl)acetate--hydrogen chloride (1/1)

Product 1

HCID 19032973(RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)octanamideYield 26.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The procedure described in Example 177 was repeated, except that (RS)-2-(4-chlorobenzenesulfonylamino)octanoic acid (1 g) and ethyl 4-aminophenylacetate hydrochloride (581 mg) were condensed in chloroform (30 ml) in the presence of triethylamine (1.66 ml) and 1-methyl-2-chloropyridinium iodide (918 mg) to obtain (RS)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)octanamide (350 mg).

Sources & evidence

ORD record
ord-234e89b3c9a5424d8132dcb359a17045
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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