Cesium carbonate → trans-N-cyanomethyl-2-[4-(4-sulfanylphenylsulfanyl)-phenylsulfanylmethyl)-cyclohexanecarboxamide

HRID 2222902Notes

Reaction equation

[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13]Br)=[O:6])#[N:2].C(=O)([O-])[O-].[Cs+].[Cs+].[SH:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1>CC(C)=O>[C:1]([CH2:3][NH:4][C:5]([C@@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:13][S:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][C:25]2[CH:26]=[CH:27][C:22]([SH:21])=[CH:23][CH:24]=2)=[CH:24][CH:23]=1)=[O:6])#[N:2]

Participants

Conditions

Temperature: 50 °C

Procedure

trans-2-Bromomethyl-cyclohexanecarboxylic acid cyanomethylamide (259 mg) and cesium carbonate (340 mg) were weighed into a 15 mL vial fitted with a stir bar and a vent cap. Acetone (3 mL) and 4-mercaptothiophenol (256 mg) were added. The reaction mixture was stirred at 50° C. overnight and then diluted with hot acetone (7 mL) and filtered through Celite™. The Celite™ was washed with hot acetone (25 mL). The filtrate and wash were combined and the solvent was removed on a rotary evaporator. Chromatography of the crude product on C-18 reverse-phase HPLC provided the title compound as a cream solid. 1H NMR (DMSO-d6): δ=8.65 (1H, t), 7.46 (2H, dd), 7.27 (4H, d), 7.21 (2H, dd), 4.12 (2H, d), 3.50 (1H, br m), 2.98 (1H, d), 2.6 (1H, m), 2.1 (2H, m), 1.7 (4H, m), 1.1 (4H, m).

Workup

customvial fitted with a stir bar
customa vent cap
filtrationfiltered through Celite™
washThe Celite™ was washed with hot acetone (25 mL)
washThe filtrate and wash
customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record: ord-5a808072489740de9010f7220e7fa100
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371747B2

Reaction notes

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