Trifluoroacetic acid → 2-((5-Formylthiazol-2-yl)amino)acetic acid

HRID 1755436Notes

Reaction equation

HRID 1755436 reaction equation
[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][C:10]([O:12]C(C)(C)C)=[O:11])=[N:5][CH:4]=1)=[O:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]([C:3]1[S:7][C:6]([NH:8][CH2:9][C:10]([OH:12])=[O:11])=[N:5][CH:4]=1)=[O:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86700084tert-Butyl 2-(5-formylthiazol-2-ylamino)acetate

Product 1

HCID 867000852-((5-Formylthiazol-2-yl)amino)acetic acidYield 181.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a magnetically stirred solution of material from Example 2 (2.19 g, 9.04 mmol) in CH2Cl2 (50 mL) is added TFA (25 mL, 324 mmol). The resulting solution is allowed to stir at room temperature for 8 h and then evaporated to dryness under a gentle stream of N2 over 18 h. The resulting tan residue is dissolved in CH2Cl2, sonicated briefly and the solvent is removed in vacuo to give 3.05 g (96%) the title compound as a tan solid as a •1.3 TFA salt by weight. LC/MS (Condition A): ret. T=0.82 min, (M+H)+ 187.00. 1H NMR (500 MHz, DMSO-d6) δ ppm 9.67 (1 H, s), 9.11 (1 H, br. s.), 8.05 (1 H, s), 4.12 (2 H, d, J=5.19 Hz).

Workup

  1. customevaporated to dryness under a gentle stream of N2 over 18 h
  2. dissolutionThe resulting tan residue is dissolved in CH2Cl2
  3. customsonicated briefly
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-bd8df1cd60f34e40bd075107ce928f02
Source dataset
uspto-grants-2015_10
Patent number
US09169295B2

Reaction notes

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