Phenyl isocyanate → PhNHCO-Leu-DTrp-betaAla-OEt

HRID 1757302Notes

Reaction equation

HRID 1757302 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].FC(C(O)=O)(F)F.[C:38]1([N:44]=[C:45]=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)(Cl)Cl>[C:38]1([NH:44][C:45]([NH:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])[CH2:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6])=[O:46])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 131719107Leu-DTrp-betaAla-OEt-TFA

Product 1

HCID 131719109PhNHCO-Leu-DTrp-betaAla-OEt

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of Leu-DTrp-βAla-OEt.TFA (40.6 mg) obtained in Example 51-(1) in chloroform (2 ml) were added TEA (20 μl) and phenyl isocyanate (15 μl) at room temperature under nitrogen. The reaction mixture was stirred for 1 h, and concentrated under reduced pressure. The residue was purified by dry column flash chromatography (Merck, Kieselgel 60) with chloroform/methanol=10/1 for elution to give the product (39.6 mg).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified
  3. dry with materialby dry column flash chromatography (Merck, Kieselgel 60) with chloroform/methanol=10/1
  4. washfor elution

Sources & evidence

ORD record
ord-4fbfc90d77654af5b206c252f3e84d51
Source dataset
uspto-grants-1995_08
Patent number
US05444152

Reaction notes

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