Hydrochloric Acid → HCID 9805626, compound

HRID 1636892Notes

Reaction equation

[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[C:15]([F:21])([F:20])[CH2:16][C:17]([OH:19])=[O:18].C([N-]C(C)C)(C)C.[Li+].Br[CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:37]2[C:36]1=[O:45].Cl>O1CCCC1>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:14](=[O:22])[C:15]([CH:16]([CH2:32][CH2:33][CH2:34][N:35]1[C:39](=[O:40])[C:38]2[C:37](=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:36]1=[O:45])[C:17]([OH:19])=[O:18])([F:21])[F:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-dibenzofuran-2-yl-3,3-difluoro-4-oxo-butyric acid (1 equivalent, Example 1) in tetrahydrofuran cooled to -78° C. is added dropwise two equivalents of lithium diisopropylamide. The solution is stirred for 30 minutes at -78° C. followed by the dropwise addition of a solution of N-(3-bromopropyl)phthalimide (1 equivalent) in tetrahydrofuran. The reaction mixture gradually warms to 0° C., at which time aqueous hydrochloric acid (HCl) (1 M) is added. The product is partitioned between ethyl acetate and water, the layers separated, and the organic portion is washed with brine, dried (MgSO4), and concentrated in vacuo. The crude product is purified using silica gel chromatography (elution with chloroform/methanol) to afford the title compound.

Workup

additionis added
customThe product is partitioned between ethyl acetate and water
customthe layers separated
washthe organic portion is washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe crude product is purified
washsilica gel chromatography (elution with chloroform/methanol)

Sources & evidence

ORD record: ord-59be1c307da14076962ccff7281f07a6
Source dataset: uspto-grants-2000_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06037361

Reaction notes

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