1,3-DI-Boc-2-methylisothiourea → HCID 178491155, compound

HRID 1934677Notes

Reaction equation

HRID 1934677 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:10]=2[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[O:12])[CH2:4][CH2:3]1.[C:32]([O:36][C:37]([NH:39][C:40](=[N:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])SC)=[O:38])([CH3:35])([CH3:34])[CH3:33]>C(O)C.[Hg]=O>[C:47]([O:46][C:44]([N:43]=[C:40]([NH:39][C:37]([O:36][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:38])[NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][C:10]=2[C:11]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[CH:16]=2)=[O:12])[CH2:4][CH2:3]1)=[O:45])([CH3:50])([CH3:49])[CH3:48]

Participants

5

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 178491154HCID 178491154, compound

Product 1

HCID 178491155HCID 178491155, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 2-(trans-4-aminocyclohexylamino)-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (300 mg) and 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (203 mg) in ethanol (20 mL) was added mercury(II) oxide (152 mg). The mixture was stirred for 2 hours at ambient temperature. The resultant precipitates were removed by filtration and the filtrate was evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with 2% methanol in chloroform. The obtained product was triturated with diisopropyl ether to give 2-{trans-4-[2,3-bis(tert-butoxycarbonyl)guanidino]cyclohexylamino}-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide as yellow powders (432 mg).

Workup

  1. customThe resultant precipitates
  2. customwere removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customThe residue was purified by a silica gel column chromatography
  5. washeluting with 2% methanol in chloroform
  6. customThe obtained product was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-7b7bf8ba522240b8a5d353ba8976fad4
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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