Triethylamine → 1-(N-(3-(4-hydroxyphenyl)propionyl)-2-aminoethyl)-4-(2-aminoethyl)imidazole

HRID 2291531Notes

Reaction equation

HRID 2291531 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:8]=[C:7]([CH2:9][CH2:10][NH:11]C(OC(C)(C)C)=O)[N:6]=[CH:5]1.C(N(CC)CC)C.C1C(=O)N([O:33][C:34]([CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=2)=O)C(=O)C1>C(Cl)Cl>[OH:44][C:41]1[CH:40]=[CH:39][C:38]([CH2:37][CH2:36][C:34]([NH:1][CH2:2][CH2:3][N:4]2[CH:8]=[C:7]([CH2:9][CH2:10][NH2:11])[N:6]=[CH:5]2)=[O:33])=[CH:43][CH:42]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 99557N-Succinimidyl-3-(4-hydroxyphenyl)propionateHCID 572371571-(2-aminoethyl)-4-(N-(tert.butyloxycarbonyl)-2-aminoethyl)imidazole

Product 1

HCID 212787501-(N-(3-(4-hydroxyphenyl)propionyl)-2-aminoethyl)-4-(2-aminoethyl)imidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The following materials are introduced into a reaction vessel: 5 mg (0.02 mmol) of compound VII dissolved in 0.5 ml methylene chloride; 2.8 μl (0.02 mmol) of triethylamine; and last 5.3 mg (0.02 mmol) of N-succinimidyl-3-(4-hydroxyphenyl)propionate dissolved in 0.5 ml of methylene chloride. The solution is stirred for 2 hours at room temperature and then evaporated. The residue is dissolved in 0.5 ml of trifluoroacetic acid, and hydrolysis is allowed to proceed for 1 hour and 15 minutes at room temperature. The solution is evaporated, the residue then being separated on a reversed-phase column PepRPC (Pharmacia AB) with an 0.1% trifluoroacetic acid - acetonitrile gradient. At about 7% acetonitrile compound XIX is eluted. The structure has been confirmed by NMR analysis, the NMR data being the following: 2H-imidazole 8.3, 5H-imidazole 7.2, O-H-hydroxyphenyl 7.1, m-H-hydroxyphenyl 6.85, 1-CH2 -imidazole 4.15, --CH2NHCO 3.55, --CH2N + H3 3.25 t, 4-CH2 -imidazole 3.05 t, p-CH2 -hydroxyphenyl 2.75 t, --CH2CO 2.5 t.

Workup

  1. additionThe following materials are introduced into a reaction vessel
  2. customevaporated
  3. dissolutionThe residue is dissolved in 0.5 ml of trifluoroacetic acid
  4. customhydrolysis
  5. waitto proceed for 1 hour and 15 minutes at room temperature
  6. customThe solution is evaporated
  7. customthe residue then being separated on a reversed-phase column PepRPC (Pharmacia AB) with an 0.1% trifluoroacetic acid - acetonitrile gradient
  8. washAt about 7% acetonitrile compound XIX is eluted

Sources & evidence

ORD record
ord-2d496ca3614042708f36c586e36ba2d3
Source dataset
uspto-grants-1989_01
Patent number
US04797370

Reaction notes

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