Water → HCID 46947723, compound

HRID 2370583Notes

Reaction equation

[OH:1]OS([O-])=O.[K+].[CH3:7][C:8]1([CH3:49])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([CH2:24][CH2:25][CH2:26][C:27]([F:33])([F:32])[C:28]([F:31])([F:30])[F:29])=[O:23])[C:11](=[O:34])[N:10]([C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[C:37]([C:44]([F:47])([F:46])[F:45])[CH:36]=2)[C:9]1=[O:48].O>C1COCC1>[CH3:7][C:8]1([CH3:49])[N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][S:22]([CH2:24][CH2:25][CH2:26][C:27]([F:32])([F:33])[C:28]([F:31])([F:30])[F:29])(=[O:1])=[O:23])[C:11](=[O:34])[N:10]([C:35]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[C:37]([C:44]([F:46])([F:47])[F:45])[CH:36]=2)[C:9]1=[O:48]

Participants

Conditions

Temperature: 23 °C

Procedure

Oxone® (566 mg, 0.93 mmole) is added to a solution of the compound of Example 2 (200 mg, 0.31 mmole) in THF (6 ml). The reaction mixture is completed with water (3 ml) and stirred at 23° C. for 3 h 30, the time necessary for the total conversion of the starting product. The mixture is then poured into water (25 ml) and extracted with AcOEt (2×25 ml). After decantation, the organic phases are combined and washed with salt water (20 ml), dried over Na2SO4, filtered and concentrated to dryness under vacuum. The evaporation residue is purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 3/7). The expected compound is obtained in the form of a colourless oil with a yield of 89% (185 mg).

Workup

extractionextracted with AcOEt (2×25 ml)
washwashed with salt water (20 ml)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated to dryness under vacuum
customThe evaporation residue is purified on a silica column (eluent: Heptane/AcOEt: 1/1 to 3/7)

Sources & evidence

ORD record: ord-b5dded4724e64b3e8ace307ec8947667
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08710091B2

Reaction notes

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