4-Iodobenzenesulfonyl chloride → 3-(Tetrahydropyran-2-yloxy)propanamide

HRID 266279Notes

Reaction equation

HRID 266279 reaction equation
C(OC(N[CH:12]([CH2:28][O:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][O:31]1)[C:13]([NH:15]C1C=CC(CC(OCC)=O)=CC=1)=[O:14])=O)C1C=CC=CC=1.IC1C=CC(S(Cl)(=O)=O)=CC=1>[Pd]>[O:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH:30]1[O:29][CH2:28][CH2:12][C:13]([NH2:15])=[O:14]

Participants

4

Reactant 2

HCID 73994-Iodobenzenesulfonyl chlorideHCID 19032873(RS)-2-(benzyloxycarbonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-(tetrahydropyran-2-yloxy)propanamide

Product 1

HCID 203933613-(Tetrahydropyran-2-yloxy)propanamideYield 307.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure described in Example 15 was repeated, except that (RS)-2-(benzyloxycarbonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)-3-(tetrahydropyran-2-yloxy)propanamide (1.0 g) was hydrogenolyzed in the presence of 10% Pd-C, and then, reacted with 4-iodobenzenesulfonyl chloride (1.31 g) to obtain (RS)-N-(4-(ethoxycarbonyl-methyl)phenyl)-2-(4-iodobenzenesulfonylamino)-N-(3-(tetrahydropyran-2-yloxy)propanamide (1.10 g).

Sources & evidence

ORD record
ord-17675e42e92f48978a6ebe92b16e83d1
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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