Acetonitrile → HCID 68311075, compound

HRID 470696Notes

Reaction equation

ClC1C=C2C([C:6]3([C@@H:15](C4C=CN=C(Cl)C=4F)[C@H:14]([C:24](N[C@H]4CC[C@H](C5OC=NN=5)CC4)=[O:25])[N:13]([C@H](C4C=CC=CC=4)[C@@H](O)C4C=CC=CC=4)C43CCC(C)(C)CC4)[C:7](=O)N2)=CC=1.[C:60](=[O:63])(O)[O-:61].[Na+].[C:65](Cl)([O:67][CH2:68][C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1)=[O:66].[C:76](#N)C>O>[CH2:68]([O:67][C:65]([NH:13][C@H:14]1[CH2:24][O:25][C@H:7]([C:60]([O:61][CH3:76])=[O:63])[CH2:6][CH2:15]1)=[O:66])[C:69]1[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=1

Participants

Conditions

Temperature: 5 °C

Procedure

The compound (0.80 g, 4.08 mmol) obtained in Step 1 above was dissolved in acetonitrile (10 ml) and water (20 ml), sodium bicarbonate (1.71 g, 30.4 mmol) and carbobenzoxy chloride (0.72 ml, 4.89 mmol) were added under ice cooling and the resulting mixture was stirred at 5° C. for 21 hours. Saturated sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane:methanol [10:1 (v/v)]. The organic layer was dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue obtained was purified by silica gel column chromatography [n-hexane:ethyl acetate=17:3→3:2 (v/v)] to give 0.97 g (81%) of the title compound as a colorless solid.

Workup

extractionfollowed by extraction with dichloromethane
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationThe solvent was concentrated under reduced pressure
customthe residue obtained
customwas purified by silica gel column chromatography [n-hexane:ethyl acetate=17:3→3:2 (v/v)]

Sources & evidence

ORD record: ord-78d0cc240e464c43a986a129210892aa
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629133B2

Reaction notes

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