1,3-DI-Boc-2-methylisothiourea → HCID 53686147, compound

HRID 363695Notes

Reaction equation

HRID 363695 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][NH2:6].[C:10]([O:14][C:15]([NH:17][C:18](=[N:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])SC)=[O:16])([CH3:13])([CH3:12])[CH3:11]>CN(C=O)C.O.C([O-])(=O)C.[Ag+]>[C:25]([O:24][C:22]([NH:21][C:18]([NH:17][C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])=[N:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([OH:1])[CH:3]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

6

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 7358943-(Aminomethyl)phenol

Product 1

HCID 53686147HCID 53686147, compound

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-hydroxybenzylamine, prepared as above (1.23 g) and N,N'-bis(tert-butoxycarbonyl)-S-methylisothiourea (2.90 g) were combined in 100 mL DMF, and silver acetate (2.9 g) was added in three portions over 30 min with mechanical stirring. The mixture became thick and a yellow color developed. After 1 hr, the mixture was diluted with 300 mL water, and the solids collected by filtration, re-suspended in dichloromethane, filtered to remove silver salts, and chromatographed on silica gel with 10% ethyl acetate in dichloromethane. Recrystallization provided the title compound as a white solid, mp 169°-172° C. (dec) (2.2 g, 61%).

Workup

  1. filtrationthe solids collected by filtration
  2. filtrationfiltered
  3. customto remove silver salts
  4. customchromatographed on silica gel with 10% ethyl acetate in dichloromethane
  5. customRecrystallization

Sources & evidence

ORD record
ord-f5f520bfcd114334895988ad6ff857e4
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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