Tyramine → N,N'-Bis(t-butoxycarbonyl)-N"-2-(4-hydroxyphenyl)ethylguanidine

HRID 363696Notes

Reaction equation

HRID 363696 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])SC)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[N:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5610TyramineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 54305970N,N'-Bis(t-butoxycarbonyl)-N"-2-(4-hydroxyphenyl)ethylguanidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N,N'-Bis(tert-butoxycarbonyl)-S-methylisothiourea (22.4 g, 77.3 mmol) is dissolved in 130 mL of THF and added dropwise under nitrogen to 10.6 g (77.3 mmol) of tyramine in 100 mL of THF at 0° C. Reaction reaches completion overnight according to TLC. The solvent is removed in vacuo. Purification on a silica gel column, eluted successively with 5% EtOAc/Hexane, 15% EtOAc/Hexane, and 35% EtOAc/Hexane, provides the title compound as a white solid, m.p. 132°-133° C. (dec.) (21.0 g, 72%).

Workup

  1. customReaction
  2. customcompletion overnight
  3. customThe solvent is removed in vacuo
  4. customPurification on a silica gel column
  5. washeluted successively with 5% EtOAc/Hexane, 15% EtOAc/Hexane, and 35% EtOAc/Hexane

Sources & evidence

ORD record
ord-0ece84ffbd4c44f2844f1bfc136346d4
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

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