Diethyl Ether → HCID 11602839, compound

HRID 1158519Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:22])[NH:4][C@H:5]([C:10]([NH:12][NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Br)[CH:16]=1)=[O:11])[C:6]([CH3:9])([CH3:8])C.CCO[CH2:26][CH3:27].C([O-])(O)=O.[Na+]>C1COCC1.CC(O[Ti](OC(C)C)(OC(C)C)OC(C)C)C>[CH2:1]([O:2][C:3](=[O:22])[NH:4][C@H:5]([C:10]([NH:12][NH:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:11])[CH:6]([CH3:8])[CH3:9])[C:27]1[CH:26]=[CH:8][CH:6]=[CH:5][CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(2S)-2-Benzyl-oxirane-N-[(1S,2R)-2-hydroxy-indan-1-yl]-2-carboxylic acid amide (0.930 g, 3.01 mmol) and compound 25 (1.23 g, 3.31 mmol) were dissolved in dry THF (40 mL), Ti(OiPr)4 (1.79 mL, 6.02 mmol) was added and the mixture was stirred at 40° C. for 2 h. Et2O (100 mL) and saturated NaHCO3 (aq., 100 mL) was added to the reaction mixture and the phases were separated. The organic phase was then washed with H2O (2×200 mL). All water phases were reextracted with CHCl3 (100 mL), and the combined organic phases were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (RP-silica, CH3CN/H2O, 50:50-70:30) affording 3 (0.95 g, 46%) as a light yellow solid.

Workup

customthe phases were separated
washThe organic phase was then washed with H2O (2×200 mL)
dry with materialthe combined organic phases were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography (RP-silica, CH3CN/H2O, 50:50-70:30)

Sources & evidence

ORD record: ord-9ae41eca5f444fa6ac2b655540e676df
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807677B2

Reaction notes

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