Phosgene → HCID 66891582, compound

HRID 456237Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH:24][C@@H:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][C@@H:26]2[OH:34])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1.C(N(CC)CC)C.[C:43](Cl)(Cl)=[O:44]>C1(C)C=CC=CC=1.CCOC(C)=O.O.[Cl-].[Na+].O>[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]1[CH:6]=[C:7]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:15][C:14]=2[CH2:23][N:24]2[C@@H:25]3[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[CH2:27][C@@H:26]3[O:34][C:43]2=[O:44])[C:8]([O:11][CH3:12])=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To {2′-[((1R,2S)-2-hydroxy-indan-1-ylamino)-methyl]-6-methoxy-4′-trifluoromethyl-biphenyl-3-yl}-acetic acid methyl ester (0.178 g, 0.37 mmol) in toluene (3 mL) was added triethylamine (0.18 mL, 1.29 mmol), and the mixture was cooled to 0° C. Phosgene (1.9M in toluene; 0.23 mL, 0.44 mmol) was added, and the reaction was stirred for 20 minutes at 0° C. The mixture was diluted with EtOAc, H2O, and brine, and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and the residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Workup

extractionthe aqueous layer was extracted with EtOAc
dry with materialThe combined organic layers were dried over MgSO4
filtrationfiltered
concentrationconcentrated
customthe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record: ord-8d2c4d6642f549d5855e3e708fc55f68
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08497381B2

Reaction notes

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