Dimethylformamide → t-butyl [(1R)-2-(3-cyanophenoxy)-1-(4-iodobenzyl)ethyl]carbamate

HRID 747735Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:17][C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([I:26])=[CH:22][CH:21]=1.CN(C)C=O>O>[C:1]([C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[O:9][CH2:17][C@H:18]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([I:26])=[CH:24][CH:25]=1)#[N:2]

Participants

Conditions

Temperature: 70 °C

Procedure

724 mg (6.08 mmol) of 3-cyanophenol and 1.12 g (8.1 mmol) of potassium carbonate were added to 1.6 g (0.60 mmol) of t-butyl [(1R)-2-chloro-1-(4-iodobenzyl)ethyl]carbamate and 25 ml of dimethylformamide, and they were stirred at 70° C. for 55 hours. The reaction liquid was diluted with water. After extraction with ethyl acetate, the organic layer was successively washed with water and saturated aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

Workup

customThe reaction liquid
extractionAfter extraction with ethyl acetate
washthe organic layer was successively washed with water and saturated aqueous NaCl solution
customThe solvent was evaporated
customthe residue was purified by the silica gel column chromatography

Sources & evidence

ORD record: ord-ead6881ae7e9418bbf9d9b7f2931aebd
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07396844B1

Reaction notes

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