Water → N-carbamimidoyl-1-[(2S)-1-hydroxy-4-phenylbutan-2-yl]imidazole-4-carboxamide

HRID 278490Notes

Reaction equation

C[O-].[Na+].Cl.[NH2:5][C:6]([NH2:8])=[NH:7].[Si]([O:16][CH2:17][C@@H:18]([N:27]1[CH:31]=[C:30]([C:32](OC)=[O:33])[N:29]=[CH:28]1)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(C(C)(C)C)(C)C.O>CO.CN(C=O)C>[OH:16][CH2:17][C@@H:18]([N:27]1[CH:31]=[C:30]([C:32]([NH:7][C:6]([NH2:8])=[NH:5])=[O:33])[N:29]=[CH:28]1)[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 28% NaOMe in methanol (583 mg) was added to an ice cooled solution of guanidine hydrochloride (307 mg) in DMF (5 ml). After 10 minutes, methyl (S)-1-[1-(tert-butyl-dimethylsilyloxy)-4-phenyl-2-butyl]imidazole-4-carboxylate (obtained in Example 6) (250 mg) in DMF (2 ml) was added to the mixture and the resulting mixture was stirred at 100° C. for 5 hours. After cooling, the reaction mixture was poured into water (30 ml) and the solution was washed with ethyl acetate. The aqueous layer was purified by HP-20 (40 cc) column chromatography eluting with water/2-propanol (9:1) and lyophilized to give (S)-1-[1-hydroxy-4-phenyl-2-butyl]imidazole-4-carbonylguanidine (55.4 mg)

Workup

temperatureAfter cooling
washthe solution was washed with ethyl acetate
customThe aqueous layer was purified by HP-20 (40 cc) column chromatography
washeluting with water/2-propanol (9:1)

Sources & evidence

ORD record: ord-70626295c19545aa8a7dfab46d9bae30
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359145B1

Reaction notes

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