1,3-DI-Boc-2-methylisothiourea → N,N-Diboc-4-(guanidinomethyl)phenol

HRID 363694Notes

Reaction equation

HRID 363694 reaction equation
O.[OH:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[C:11]([O:15][C:16]([NH:18][C:19](=[N:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])SC)=[O:17])([CH3:14])([CH3:13])[CH3:12]>C1COCC1>[C:26]([O:25][C:23]([NH:22][C:19]([NH:18][C:16]([O:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:17])=[N:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([OH:2])=[CH:4][CH:5]=1)=[O:24])([CH3:29])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 5466031,3-DI-Boc-2-methylisothioureaHCID 675697984-Hydroxybenzylamine hydrate

Product 1

HCID 54472066N,N-Diboc-4-(guanidinomethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-hydroxybenzylamine hydrate, prepared as above (5.33 g) and N,N'-Bis(tert-butoxycarbonyl)-S-methylisothiourea (10.96 g) were combined in 150 mL THF, and stirred at reflux for 4 hr. The mixture was concentrated, and the crude product chromatographed on silica gel with 10% ethyl acetate in dichloromethane. Recrystallization from methanol-water provided the title compound as a white solid, mp 187°-189° C. (10 g, 70%).

Workup

  1. temperatureat reflux for 4 hr
  2. concentrationThe mixture was concentrated
  3. customthe crude product chromatographed on silica gel with 10% ethyl acetate in dichloromethane
  4. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-79aa7583206a4ae68c6f52b8de56000c
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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