Phenylacetic Acid → HCID 131731594, compound

HRID 404120Notes

Reaction equation

[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CCOCC1.ClC(OCC(C)C)=O.[NH2:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:41]=[C:40]3[C:36]([CH2:37][N:38]([C@@H:43]([CH:48]([CH3:50])[CH3:49])[C:44]([O:46][CH3:47])=[O:45])[C:39]3=[O:42])=[CH:35][CH:34]=2)=[CH:29][CH:28]=1>C1COCC1.CCOC(C)=O>[CH3:49][CH:48]([CH3:50])[C@H:43]([N:38]1[CH2:37][C:36]2[C:40](=[CH:41][C:33]([C:30]3[CH:29]=[CH:28][C:27]([NH:26][C:8](=[O:10])[CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:32][CH:31]=3)=[CH:34][CH:35]=2)[C:39]1=[O:42])[C:44]([O:46][CH3:47])=[O:45]

Participants

Conditions

Temperature: -25 °C

Procedure

To a solution of 2-phenylacetic acid (150 mg, 1.102 mmol) in THF (5 mL) was added N-methylmorpholine (0.182 mL, 1.653 mmol) and cooled to −20 to −30° C. To this solution was added isobutyl chloroformate (0.145 mL, 1.102 mmol) and the reaction mixture was stirred at −20° C. for 30 min. To the reaction mixture, a solution of compound of example 6 (336 mg, 0.992 mmol) in THF (2.5 mL) was added and stirred at room temperature for 2-3 h. After completion of the reaction, EtOAc was added to the reaction mixture and washed with brine water. The organic extract was dried over anhydrous sodium sulfate and concentrated to obtain a crude material, which was purified by column chromatography (silicagel, 30% ethyl acetate in chloroform).

Workup

stirringstirred at room temperature for 2-3 h
additionwas added to the reaction mixture
washwashed with brine water
extractionThe organic extract
dry with materialwas dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-7ab607dfd2884339bed8ef463bdbf172
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748426B2

Reaction notes

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