Trifluoroacetic acid → 2-[[2-Aminothiazol-4-yl]acetylamino]4-thiazoleacetic acid, ethyl ester

HRID 1275892Notes

Reaction equation

HRID 1275892 reaction equation
CC(C)(OC([NH:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=2)=[O:15])[N:12]=1)=O)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]1[S:9][CH:10]=[C:11]([CH2:13][C:14]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[N:21]=2)=[O:15])[N:12]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 867561272-[[2-[1,1-Dimethylethoxycarbonylamino]thiazol-4-yl]acetylamino]-4 thiazoleacetic acid, ethyl ester

Product 1

HCID 867561282-[[2-Aminothiazol-4-yl]acetylamino]4-thiazoleacetic acid, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product from step (i) (0.8 g) in dry dichloromethane (15 ml) was treated with trifluoroacetic acid (5 ml). After 6 hours at room temperature the mixture was azeotroped with toluene. The residue was dissolved in ethyl acetate and washed with aqueous sodium bicarbonate. The organic solution was dried (MgSO4) and evaporated under reduced pressure. The residue was triturated with ethyl acetate/isohexanes and filtered. Yield 0.53 g.

Workup

  1. customAfter 6 hours at room temperature the mixture was azeotroped with toluene
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was triturated with ethyl acetate/isohexanes
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ccecad2251f348d0bdd70b9b959e4247
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Reaction notes

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