Water → 3-[1-(4-isopropyl-benzenesulfonyl)-1H-indol-5-yl]-azetidine-1-carboxylic acid tert-butyl ester

HRID 1890377Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

3-(1H-Indol-5-yl)-azetidine-1-carboxylic acid tert-butyl ester (135 mg, 0.5 mmol) was dissolved in DMF (10 ml) and cooled to 0° C. Sodium hydride (35.7 mg, 0.74 mmol) was added, and the reaction mixture was stirred for 1 hour at 0° C. 4-Isopropyl-benzenesulfonyl chloride (98 μl, 0.55 mmol) was added slowly to the reaction mixture. Stirring was continued for 10 minutes. Cold water (100 ml) was added to the reaction mixture, and it was extracted twice with diethyl ether (80 ml). The organic layer was dried over magnesium sulphate, filtered, and the solvent was evaporated under reduced pressure to give a crystalline solid (75 mg, 33%). ESI-MS [m/z]: 355.15 [M-(Boc)+H]+.

Workup

stirringStirring
waitwas continued for 10 minutes
extractionwas extracted twice with diethyl ether (80 ml)
dry with materialThe organic layer was dried over magnesium sulphate
filtrationfiltered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-df8747c6e9914bafb9c13775fcef6b9d
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507469B2

Reaction notes

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