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

HRID 2388016Notes

Reaction equation

HRID 2388016 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:5]=[N:6][C:7]=1[CH3:8].[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:15]([O:14][C:13]([NH:12][CH2:11][CH2:10][CH2:9][C:4]1[CH:3]=[C:2]([NH:1]/[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:7]([CH3:8])=[N:6][CH:5]=1)=[O:19])([CH3:16])([CH3:18])[CH3:17]

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-095228c6e35f4a63b9fef7e1587790f3
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

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