3-Nitrobenzenesulfonyl chloride → (2S,4R)-4-(3-Nitro-benzenesulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 38042

Reaction equation

[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[N+:18]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)(=[O:28])=[O:29])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

Participants

Conditions

Temperature: 5 °C

Procedure

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.0 g) was dissolved in DCM (50 mL) and 3-nitrobenzenesulfonyl chloride (4.8 g) was added. This solution was cooled to 5° C. and the TEA (8.52 mL) was carefully added. The reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtrated and evaporated to dryness to yield a light brown amorphous solid (9.05 g). MS: m/z=431.4 [M+H]+.

Workup

extractionThe reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL)
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltrated
customevaporated to dryness

Sources & evidence

ORD record: ord-ed6f79568ea1451898ce3a8046113a50
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524710B2

Linked notes

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