Trifluoroacetic acid → HCID 45117288, compound

HRID 343321Notes

Reaction equation

HRID 343321 reaction equation
FC(F)(F)C(O)=O.C(OC([NH:15][C@H:16]([C:26]([OH:28])=[O:27])[CH2:17][C:18]1[CH:23]=[CH:22][N:21]=[C:20]([C:24]#[N:25])[CH:19]=1)=O)(C)(C)C>ClCCl>[C:24]([C:20]1[CH:19]=[C:18]([CH2:17][C@@H:16]([C:26]([OH:28])=[O:27])[NH2:15])[CH:23]=[CH:22][N:21]=1)#[N:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53646148HCID 53646148, compound

Product 1

HCID 45117288HCID 45117288, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 ml) was added dropwise to a stirred, ice-cooled solution of N-t-butoxycarbonyl-3-(2-cyano-4-pyridyl)-(S)-alanine (Preparation 12; 1.6 g 5.5 mmol) in dichloromethane (10 ml) and the resulting solution stirred for 3 hours at the same temperature then evaporated under reduced pressure. The residue was dissolved in water (5 ml) and the pH of the solution adjusted to 7 with 1M aqueous sodium hydroxide solution before purification by ion-exchange chromatography on Bio Rad AG50W X-8 (H+ form) resin, using an elution gradient of pyridine:water (0:100 to 10:90), to give the title compound (1.0 g) as a white solid. Rf 0.17 (SS 13), m/e 192.

Workup

  1. customthen evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (5 ml)
  3. customthe pH of the solution adjusted to 7 with 1M aqueous sodium hydroxide solution before purification by ion-exchange chromatography on Bio Rad AG50W

Sources & evidence

ORD record
ord-7e08d359967e43ef922132c5580b8bd6
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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