1,3-Bis(benzyloxycarbonyl)-2-methylisothiourea → HCID 178432740, compound

HRID 1892215Notes

Reaction equation

HRID 1892215 reaction equation
[C:1]([O:5][C:6](=[O:19])[NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH3:18])=[C:15]([NH2:17])[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:27][C:28]([NH:30][C:31](=[N:34][C:35]([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36])SC)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)Cl.[Hg](Cl)Cl>[C:1]([O:5][C:6]([NH:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[C:15]([NH:17]/[C:31](/[NH:34][C:35](=[O:36])[O:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[N:30]/[C:28](=[O:29])[O:27][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:14]([CH3:18])=[N:13][CH:12]=1)=[O:19])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 68222687Tert-butyl [3-(5-amino-6-methylpyridin-3-yl)propyl]carbamate

Product 1

HCID 178432740HCID 178432740, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[3-(5-amino-6-methylpyridin-3-yl)propyl]carbamate (2.99 g, 11.3 mmol), 1,3-bis(benzyloxycarbonyl)-2-methyl-2-thiopseudourea (3.41 g, 9.51 mmol), and mercury(II) chloride (3.37 g, 12.4 mmol) in DCM (100 mL) was added TEA (5.19 mL, 37.3 mmol) dropwise via syringe. The reaction mixture was allowed to stir at rt overnight. The reaction mixture was filtered over a pad of Celite® and the resulting filtrate was concentrated. The residue was purified by column chromatography to give dibenzyl {(Z)-[(5-{3-[(tert-butoxycarbonyl)amino]propyl}-2-methylpyridin-3-yl)amino]methylylidene}biscarbamate (3.34 g, 61%) as a white solid. LCMS (FA): Rt=1.90 min, m/z=576.0 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered over a pad of Celite®
  2. concentrationthe resulting filtrate was concentrated
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3d76bc88fd0d48dd82cb053183e48a2d
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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