Tert-butyl acetoacetate → (2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate

HRID 1697650Notes

Reaction equation

HRID 1697650 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][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[CH2:7][NH:6]1)=[O:4].[C:21](OC(C)(C)C)(=[O:26])[CH2:22][C:23]([CH3:25])=[O:24]>>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[Cl:20])(=[O:12])=[O:11])[CH2:7][N:6]1[C:21](=[O:26])[CH2:22][C:23](=[O:24])[CH3:25])=[O:4]

Participants

3

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 66770675(2S,4R)-4-(2-chloro-4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 86646855(2S,4R)-methyl 4-(2-chloro-4-fluorophenylsulfonyl)-1-(3-oxobutanoyl)pyrrolidine-2-carboxylate

Procedure

In analogy to the procedure described in example 192f, (2S,4R)-4-(2-chloro-4-fluoro-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with tert-butyl acetoacetate to give the title compound as yellow foam. MS (ESI): m/z=406.3 [M+H]+.

Sources & evidence

ORD record
ord-5187f464213a4f42ac2ab4d366890d5d
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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