Trifluoroacetic acid → HCID 178511786, compound

HRID 980383Notes

Reaction equation

HRID 980383 reaction equation
C(OC([NH:8][C@H:9]([C:16]([N:18]1[CH2:28][CH2:27][CH2:26][C@H:19]1[C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][C@H:9]([C:16]([N:18]1[CH2:28][CH2:27][CH2:26][C@H:19]1[C:20]([NH:22][CH2:23][CH2:24][OH:25])=[O:21])=[O:17])[CH2:10][C:11]1[N:15]=[CH:14][NH:13][CH:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178454167HCID 178454167, compound

Product 1

HCID 178511786HCID 178511786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 25 ml of methylene chloride was dissolved 790 mg of compound (51) and then 20 ml of trifluoroacetic acid was added dropwise to the solution at 0° C. to 5° C. After stirring the mixture for 2.5 hours in an ice-bath, the reaction mixture was concentrated to dryness under reduced pressure. Furthermore, the product was azeotropically dried several times using toluene and the residue was triturated with dry ether to provide powder of L-histidyl-N-(2-hydroxyethyl)-L-prolinamide.2-trifluoroacetate with a quantitative yield.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness under reduced pressure
  2. customthe residue was triturated with dry ether

Sources & evidence

ORD record
ord-014cb1bfa70a4c0d9e27a16206e4be0d
Source dataset
uspto-grants-1987_01
Patent number
US04636567

Reaction notes

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