Methanesulfonyl chloride → 4-(2-Chloro-2-oxazolo[4,5-c]pyridin-2-ylethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 217185Notes

Reaction equation

CS([Cl:5])(=O)=O.[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20](O)[C:21]2[O:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][C:24]=3[N:29]=2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]>N1C=CC=CC=1>[C:6]([O:10][C:11]([N:13]1[CH2:18][CH2:17][CH:16]([CH2:19][CH:20]([Cl:5])[C:21]2[O:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][C:24]=3[N:29]=2)[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

MsCl (29 μL, 0.38 mmol) was added to a stirred solution of 4-(2-hydroxy-2-oxazolo[4,5-c]pyridin-2-yl-ethyl)piperidine-1-carboxylic acid tert-butyl ester (Preparation 7, 110 mg, 0.32 mmol) in anhydrous pyridine (5 mL) at 0° C. After 1 h, more MsCl (29 μL, 0.38 mmol) was added, then the mixture was stirred at 0° C. for an additional 1 h, before being heated under reflux for 1 h. The reaction was concentrated under reduced pressure, then the residue was purified by flash chromatography (EtOAc-IH, 7:3) to furnish the title compound: RT=3.57 min; m/z (ES+)=310.0 [M+2H-t-Bu]+.

Workup

temperaturebefore being heated
temperatureunder reflux for 1 h
concentrationThe reaction was concentrated under reduced pressure
customthe residue was purified by flash chromatography (EtOAc-IH, 7:3)

Sources & evidence

ORD record: ord-ce22e98802404569ada2cc707e7c3afc
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193359B2

Reaction notes

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