3-Oxo-3-(tetrahydro-pyran-4-yl)-propionic Acid Tert-butyl Ester → (2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-propionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697666Notes

Reaction equation

HRID 1697666 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4].C([O:27][C:28](=O)[CH2:29][C:30](=[O:37])[CH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)(C)(C)C>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:20])[F:21])(=[O:11])=[O:12])[CH2:7][N:6]1[C:28](=[O:27])[CH2:29][C:30](=[O:37])[CH:31]1[CH2:36][CH2:35][O:34][CH2:33][CH2:32]1)=[O:4]

Participants

3

Reactant 2

HCID 231440503-Oxo-3-(tetrahydro-pyran-4-yl)-propionic Acid Tert-butyl EsterHCID 66771131(2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 86646856(2S,4R)-1-[3-oxo-3-(tetrahydro-pyran-4-yl)-propionyl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192f, (2S,4R)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192e) was reacted with 3-oxo-3-(tetrahydro-pyran-4-yl)-propionic acid tert-butyl ester to give the title compound as yellow foam. MS (ESI): m/z=492.2 [M+H]+.

Sources & evidence

ORD record
ord-2d357f45b99e4017b1da85be1b87af34
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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