Potassium Iodide → 2-(Benzhydrylidene-amino)-3-(2-fluoro-5-methoxy-phenyl)-propionic acid tert-butyl ester

HRID 1242859Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[F:11].[C:12]([O:16][C:17](=[O:33])[CH2:18][N:19]=[C:20]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:15])([CH3:14])[CH3:13].[I-].[K+].[OH-].C([N+](C)(C)C)C1C=CC=CC=1>O1CCOCC1.O>[C:12]([O:16][C:17](=[O:33])[CH:18]([N:19]=[C:20]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[F:11])([CH3:15])([CH3:13])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (10° C.) stirred solution of 2-fluoro-5-methoxybenzyl bromide (35, 50 mg, 0.23 mmol), t-butylglycinate Schiff base 3 (68 mg, 0.23 mmol) and potassium iodide (4.2 mg, 0.05 mmol) in dioxane (2.0 mL) was added dropwise over 30–45 min. benzyltrimethylammonium hydroxide (0.069 mL, 0.23 mmol, 40% aqueous). The reaction mixture was then brought to room temperature and stirred for an additional 3 h. After cooling to 0° C., water (2.0 mL) was added and the mixture was extracted with toluene (6×10 mL). The organic extracts were washed with water (20 mL) and dried over sodium sulfate. Evaporation of the solvent afforded a colorless oil, which was not purified (33%) and the alkylated product 40 was not obtained.

Workup

customwas then brought to room temperature
extractionthe mixture was extracted with toluene (6×10 mL)
washThe organic extracts were washed with water (20 mL)
dry with materialdried over sodium sulfate
customEvaporation of the solvent
customafforded a colorless oil, which
customwas not purified (33%)

Sources & evidence

ORD record: ord-f8b21789dbda471b9ef9755bbf6ad217
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115766B2

Reaction notes

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