Cesium carbonate → HCID 67362914, compound

HRID 1183177Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C@H:6]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([OH:22])[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[N:18]=1)=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH3:2].FC1C=CC=CC=1N1C(O)=CC(C(O)=O)=N1.N[C@H](C1C=CC=CC=1C)CC(OCC)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:69][C:70]1([CH3:74])[CH2:73][O:72][CH2:71]1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:30])[CH2:5][C@H:6]([NH:14][C:15]([C:17]1[CH:21]=[C:20]([O:22][CH2:69][C:70]2([CH3:74])[CH2:73][O:72][CH2:71]2)[N:19]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[F:29])[N:18]=1)=[O:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH3:13])[CH3:2]

Participants

Conditions

Temperature: 65 °C

Procedure

101 mg (0.245 mmol) of (S)-3-{[1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionic acid ethyl ester (prepared from 1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid and ethyl (S)-3-amino-3-(2-methyl-phenyl)-propionate analogously as described in synthesis example 2) were dissolved in 3 ml of DMF, and 160 mg (0.5 mmol) of cesium carbonate and 41.3 mg (0.245 mmol) of 3-bromomethyl-3-methyl-oxetane were added. The mixture was stirred for 4 h at 65° C. After evaporation of the solvent the residue was subjected to an aqueous work-up with EA and 10% aqueous solution of citric acid. After removal of the solvent from the organic phase 100 mg (82%) of the product are obtained.

Workup

customas described in synthesis example 2)
customAfter evaporation of the solvent the residue
customAfter removal of the solvent from the organic phase 100 mg (82%) of the product
customare obtained

Sources & evidence

ORD record: ord-132f037d98284b49bdc95c541086d538
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664257B2

Reaction notes

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