Chlorosulfonic acid → HCID 131724895, compound

HRID 2182860Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:33])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Cl:35][S:36](O)(=[O:38])=[O:37]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([CH2:13][CH2:14][O:15][C:16](=[O:34])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[O:33])[CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:36]([Cl:35])(=[O:38])=[O:37])=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 4-(3-isopropylphenoxyactamido)butyric acid 2-(3-nitrobenzenesulfonyl)ethyl ester (Intermediate 25, 4.8 g, 9.75 mmol) and 2 mL of CH2Cl2 was added drop-wise ClSO3H (3.3 mL, 5.8 g, 50 mmol) at 0° C. with vigorous stirring. The mixture was stirred at 0° C. for 40 min. and then was poured onto crushed ice with vigorous stirring resulting in a thick mass. This was extracted with CH2Cl2. The organic layers were dried, and concentrated under reduced pressure. The residual oil was passed through a short silica gel column to remove material that was not moving on TLC. The eluent was concentrated to give Intermediate 26 (3.3 g, 57%) as a light brown foam.

Workup

additionwas poured
customonto crushed ice
stirringwith vigorous stirring
customresulting in a thick mass
extractionThis was extracted with CH2Cl2
customThe organic layers were dried
concentrationconcentrated under reduced pressure
customto remove material that
concentrationThe eluent was concentrated

Sources & evidence

ORD record: ord-2945565f58554631bf5c62fafe9c6b3a
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06897227B2

Reaction notes

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