Water → HCID 19360603, compound

HRID 376984Notes

Reaction equation

[H-].[Na+].[CH2:3]([SH:7])[CH2:4][CH2:5][SH:6].[CH2:8]([C:15]([N:33]([CH3:35])[CH3:34])([CH2:31][CH3:32])[C:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27](Br)=[CH:26][CH:25]=2)=[CH:20][CH:19]=1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CN(C)C=O>[CH2:8]([C:15]([N:33]([CH3:35])[CH3:34])([CH2:31][CH3:32])[C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:29]=[CH:28][C:27]([S:6][CH2:5][CH2:4][CH2:3][SH:7])=[CH:26][CH:25]=2)=[CH:22][CH:23]=1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

9.2 mmol of sodium hydride are suspended in 40 ml of dry dimethylformamide and 2.3 ml (23 mmol) of 1,3-propanedithiol are added dropwise. Then 2.0 g (4.6 mmol) of 2-benzyl-1-(4'-bromo-biphenyl-4-yl)-2-dimethylamino-butan-1-one (prepared by the method described in U.S. Pat. No. 5,534,629) in 60 ml of dimethylformamide are added dropwise. After stirring the solution at 100° C. for 2 h, the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (10:90) as an eluent. The structure of the product is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 0.72 (t, 3H), 1.37 (t, 1H), 1.84-2.01 (m, 3H), 2.09 (dq, 1H), 2.40 (s, 6H), 2.68 (dt, 2H), 3.10 (t, 2H), 3.23 (s, 2H), 7.15-7.29 (m, 5H), 7.41 (d, 2H), 7.55-7.62 (m, 4H), 8.41 (d, 2H).

Workup

extractionThe crude product is extracted with methylene chloride
washwashed with water
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (10:90) as an eluent

Sources & evidence

ORD record: ord-428ea6292039407cb9f4bd9a704afe5e
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022906

Reaction notes

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