Trifluoroacetic acid → HCID 67126429, compound

HRID 2273793Notes

Reaction equation

HRID 2273793 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[NH:14][C@@H:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1)([O-:3])=[O:2].FC(F)(F)C(O)=O>ClCCl>[N+:1]([C:4]1[CH:9]=[C:8]([S:10]([NH2:11])(=[O:12])=[O:13])[CH:7]=[CH:6][C:5]=1[NH:14][C@@H:15]1[CH2:19][CH2:18][NH:17][CH2:16]1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67126563HCID 67126563, compound

Product 1

HCID 67126429HCID 67126429, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of EXAMPLE 428B (2.018 g) in anhydrous dichloromethane (25 mL) was cooled in an ice bath and 2,2,2-trifluoroacetic acid (20 mL) was added. After stirring 15 minutes, the ice bath was removed and the reaction was allowed to come to ambient temperature over 2 hours. The reaction mixture was concentrated and the residue was dissolved in water and basified with aqueous sodium carbonate solution. The mixture was extracted repeatedly with 10% methanol in methylene chloride and the organics were concentrated to provide the title compound.

Workup

  1. customthe ice bath was removed
  2. waitto come to ambient temperature over 2 hours
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue was dissolved in water and basified with aqueous sodium carbonate solution
  5. extractionThe mixture was extracted repeatedly with 10% methanol in methylene chloride
  6. concentrationthe organics were concentrated

Sources & evidence

ORD record
ord-b7b8e369547a4332b651c9853d833fcc
Source dataset
uspto-grants-2015_09
Patent number
US09125913B2

Reaction notes

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