Triethylamine → N,N'-Bis(t-butoxycarbonyl)-N"-3-(4-hydroxy-phenyl)propylguanidine

HRID 363697Notes

Reaction equation

HRID 363697 reaction equation
Cl.[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1.[C:13]([O:17][C:18]([NH:20][C:21](=[N:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])SC)=[O:19])([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Ag+]>[C:28]([O:27][C:25]([NH:24][C:21]([NH:20][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[N:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=1)=[O:26])([CH3:31])([CH3:30])[CH3:29]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 128228064-(3-Aminopropyl)phenol hydrochloride

Product 1

HCID 53657718N,N'-Bis(t-butoxycarbonyl)-N"-3-(4-hydroxy-phenyl)propylguanidine

Reagents, catalysts & solvents 3

HCID 11246Silver acetateCatalyst2×HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Silver acetate (1.3 g) was added to a solution of 3-(4-hydroxyphenyl)propylamine hydrochloride (1.2 g) and N,N'-Bis(tert-butoxycarbonyl)-S-methylisothiourea (1.86 g) in DMF (10 mL) containing triethylamine (3.0 g). The mixture was stirred for 3 hr, and an additional 1.0 g silver acetate was added. After one hour, the mixture was diluted with ethyl acetate, filtered through Celite, washed with water, dried over magnesium sulfate, and the solution evaporated. Chromatography on silica gel with 20% ethyl acetate in hexane provided the title compound as a white solid, mp 142°-144° C. (dec) after recrystallization from hexane-ethyl acetate (2.1 g, 77%).

Workup

  1. waitAfter one hour
  2. filtrationfiltered through Celite
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. customthe solution evaporated

Sources & evidence

ORD record
ord-fc71a32edc1b461882de129f32d46cdb
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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