Sodium Cyanide → HCID 86695203, compound

HRID 1504046Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][C:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:26])[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=O)=O.[C-:35]#[N:36].[Na+]>CS(C)=O.CN(C)C1C=CN=CC=1>[C:35]([CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][C:23]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:31])([CH3:33])[CH3:32])([CH3:26])[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)#[N:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To a 50-mL round-bottom flask containing a solution of tert-butyl N-(4-[[(3S)-3-[(methanesulfonyloxy)methyl]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate (1.0 g, 1.95 mmol, 1.00 equiv) in DMSO (12 mL) was added NaCN (479 mg, 9.78 mmol, 5.00 equiv) and 4-dimethylaminopyridine (30 mg, 0.25 mmol, 0.13 equiv) and the solution was stirred for 2.5 h at 80° C. After cooling, the reaction was then quenched by the addition of water, extracted with 3×100 mL of ethyl acetate. The organic layers were combined, washed with brine, dried over sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/2) to give the desired tert-butyl N-(4-[[(3R)-3-(cyanomethyl)-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-12-yl]oxy]-1-methylcyclohexyl)carbamate (830 mg, 96%) as a white solid.

Workup

temperatureAfter cooling
customthe reaction was then quenched by the addition of water
extractionextracted with 3×100 mL of ethyl acetate
washwashed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-05ce6def70d945d7a11ad52482810843
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

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