Tetrahydrofuran → HCID 69623716, compound

HRID 890930Notes

Reaction equation

[CH2:1]([S:4]([NH:7][C@@H:8]([C:13]([NH:15][C@H:16]([C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=1)=[O:21])[CH2:17][NH:18][CH3:19])=[O:14])[C@@H:9]([CH2:11][CH3:12])[CH3:10])(=[O:6])=[O:5])[CH2:2][CH3:3].O1CCCC1.[O-:37][C:38]#[N:39].[K+]>O>[CH2:1]([S:4]([NH:7][C@@H:8]([C:13]([NH:15][C@H:16]([C:20]([NH:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=1)=[O:21])[CH2:17][N:18]([C:38]([NH2:39])=[O:37])[CH3:19])=[O:14])[C@@H:9]([CH2:11][CH3:12])[CH3:10])(=[O:6])=[O:5])[CH2:2][CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-(propylsulfonyl)-D-isoleucyl-3-(methylamino)-N1-(4-cyanobenzyl)-L-alaninamide (500 mg, 1.0 mmol) in water (1.3 ml)/tetrahydrofuran (3 ml), potassium cyanate (243 mg, 3 mmol) was added under stirring at 50° C. and then further stirred under the same conditions. After stirring for 3 hours, water was added to the reaction mixture, which was then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate. Magnesium sulfate was filtered off and the filtrate was concentrated under reduced pressure to give N-(propylsulfonyl)-D-isoleucyl-3-[(aminocarbonyl)(methyl)amino]-N1-(4-cyanobenzyl)-L-alaninamide (430 mg, 0.87 mmol; yield 87%).

Workup

stirringfurther stirred under the same conditions
stirringAfter stirring for 3 hours
extractionwas then extracted with ethyl acetate
dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
filtrationMagnesium sulfate was filtered off
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-4ad74b1acf7040bd96cb9f6e56f0d6db
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07001887B2

Reaction notes

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