Trifluoroacetic acid → HCID 23282568, compound

HRID 369898Notes

Reaction equation

HRID 369898 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[C:21]([C:23](=[O:33])[C:24]#[C:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH:20]=[CH:19][C:4]=1[O:5][CH2:6][C:7]([NH:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:8].FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:22]=[C:21]([C:23](=[O:33])[C:24]#[C:25][C:26]([OH:28])=[O:27])[CH:20]=[CH:19][C:4]=1[O:5][CH2:6][C:7]([NH:9][C:10]1[S:11][C:12]2[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23282619HCID 23282619, compound

Product 1

HCID 23282568HCID 23282568, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[2-methoxy-4-(3-t-butoxycarbonylpropioloyl)phenoxymethylcarbonylamino]benzothiazole (0.5 g) in methylene chloride (30 ml) is added trifluoroacetic acid (10 ml), and the mixture is stirred at room temperature for 4 hours. The mixture is concentrated, and to the residue is added methylene chloride. The mixture is stirred, and the precipitated crystals are collected by filtration, and recrystallized from dichloromethane-trifluoroacetic acid to give 2-[2-methoxy-4-(3-carboxypropioloyl)phenoxymethylcarbonylamino]-benzothiazole (0.26 g) as brown powder.

Workup

  1. concentrationThe mixture is concentrated
  2. additionto the residue is added methylene chloride
  3. stirringThe mixture is stirred
  4. filtrationthe precipitated crystals are collected by filtration
  5. customrecrystallized from dichloromethane-trifluoroacetic acid

Sources & evidence

ORD record
ord-f048070fb6064734bc718af11e0112ee
Source dataset
uspto-grants-2000_10
Patent number
US06140330

Reaction notes

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