Hydrochloric Acid → HCID 66818042, compound

HRID 1754909Notes

Reaction equation

CC(C)([O-])C.[K+].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]([C:31](=[O:33])[NH2:32])([NH:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=2[F:29])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].Cl>CC(O)(C)C>[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][C:17]2([N:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=3[F:29])[NH:32][C:31]2=[O:33])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 40 °C

Procedure

Potassium t-butoxide (1.01 g, 8.97 mmol) was added to a solution of 4-carbamoyl-4-(3-chloro-2-fluoro-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (1.20 g, 2.99 mmol) in tBuOH (30.0 ml) at room temperature, and the mixture was stirred at 40° C. for six hours. The reaction mixture was adjusted to pH 6 by adding 2 N HCl and then extracted with AcOEt three times. The organic layers were sequentially washed with H2O (×2) and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (hexane/AcOEt=90:10→50:50) to give 2-(3-chloro-2-fluoro-phenyl)-4-oxo-1,3,8-triaza-spiro[4.5]dec-1-ene-8-carboxylic acid tert-butyl ester as a colorless form (1.13 g, 99%).

Workup

extractionextracted with AcOEt three times
washThe organic layers were sequentially washed with H2O (×2) and saturated brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography (hexane/AcOEt=90:10→50:50)

Sources & evidence

ORD record: ord-945d56844472460a9abd01adaee15887
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169254B2

Reaction notes

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