Cesium carbonate → HCID 69202227, compound

HRID 2220648Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CS(O[CH2:24][C@H:25]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:26])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[C:31]([O:30][C:28]([NH:27][C@H:25]([CH3:26])[CH2:24][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:29])([CH3:34])([CH3:33])[CH3:32]

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of ethyl 4′-hydroxybiphenyl-4-carboxylate (1.63 g), (R)-(+)-2-(tert-butoxycarbonylamino)propyl methanesulfonate (1.93 g), and cesium carbonate (2.70 g) in N,N-dimethylformamide (18 mL) was stirred at 50° C. for 21 hrs. The reaction mixture was diluted with ethyl acetate, washed with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by aminopropyl silica gel flash column chromatography (eluent: n-hexane/ethyl acetate=1/1) to afford ethyl 4′-[(R)-2-(tert-butoxycarbonylamino)propyloxy]biphenyl-4-carboxylate (2.93 g).

Workup

washwashed with water and brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by aminopropyl silica gel flash column chromatography (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record: ord-61cc5ad85d054e5fa05a907d85e9e836
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417169B2

Reaction notes

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