Water → HCID 66650519, compound

HRID 420059Notes

Reaction equation

[C:1]([NH:8][S:9]([CH:12]1[CH2:14][CH2:13]1)(=[O:11])=[O:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li]CCCC.Br[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[OH2:28]>C1COCC1.CCOC(C)=O>[C:1]([NH:8][S:9]([C:12]1([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:14][CH2:13]1)(=[O:10])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: -80 °C

Procedure

To a stirred solution of compound 77 (500 mg, 2.26 mmol) in anhydrous THF (5 mL) at −80° C. was added nBuLi (2.26 mL, 5.65 mmol) dropwise. The mixture was stirred at −80° C. for 10 min and bromomethylbenzene (271 μL, 3.39 mmol) was added dropwise at −80° C. The mixture was then allowed to warm up to −30° C. Water was then slowly added followed by EtOAc. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (EtOAc/DCM) to yield compound 78 as a white powder in 30% yield.

Workup

temperatureto warm up to −30° C
dry with materialOrganics were dried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
custompurified by chromatography on silica gel (EtOAc/DCM)

Sources & evidence

ORD record: ord-40a77c5613c2488a82384c8d5493c46b
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093379B2

Reaction notes

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