Sodium Hydroxide → tert-butyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester

HRID 2120246

Reaction equation

[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:8][CH2:9][CH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH2:13][C:14](=[O:20])[NH:15]2.[OH-].[Na+]>O1CCCC1.CN(C)C=O.N1C=CC=CC=1>[O:20]=[C:14]1[CH2:13][C:12]2[C:16](=[CH:17][CH:18]=[CH:19][C:11]=2[CH2:10][CH2:9][O:8][C:6](=[O:7])[NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])[NH:15]1

Participants

Conditions

Temperature: 80 °C

Procedure

Tert-butyl isocyanate (0.685 mL, 6 mmol) was added dropwise to a stirred mixture of 4-(2-hydroxy-ethyl)-1,3-dihydro-indol-2-one (709 mg, 4 mmol) in tetrahydrofuran (8 mL), dimethylforamide (2 mL) and pyridine (3 drops). The mixture was heated at 70° C. for 15 hours and 80° C. for 39 hours. 0.457 mL of tert-butyl isocyanate was added to the reaction and continued to heat at 90° C. for 24 hours. More tert-butyl isocyanate (0.457 mL) was added and continued to heat at 90° C. for 37 hours. The reaction was cooled, poured into 1 N sodium hydroxide solution (100 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with 1 N hydrochloric acid (100 mL) and brine, dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from methanol/ethyl acetate/hexane to give 130 mg (12%) of tert-butyl-carbamic acid 2-(2-oxo-2,3-dihydro-1H-indol-4-yl)-ethyl ester.

Workup

temperatureto heat at 90° C. for 24 hours
temperatureto heat at 90° C. for 37 hours
temperatureThe reaction was cooled
extractionextracted with ethyl acetate (200 mL)
washThe organic layer was washed with 1 N hydrochloric acid (100 mL) and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customThe residue was recrystallized from methanol/ethyl acetate/hexane

Sources & evidence

ORD record: ord-c893304840fa4d81a61638cf54280fcb
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689806B1

Linked notes

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