Trifluoroacetic acid → HCID 178433201, compound

HRID 378993Notes

Reaction equation

HRID 378993 reaction equation
[NH:1]([C:5]1[S:6][C:7]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=2)[O:17][CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[O:12])=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3].FC(F)(F)C(O)=O>C(Cl)Cl>[NH:1]([C:5]1[S:6][C:7]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([CH:26]=[CH:27][CH:28]=2)[O:17][CH2:18][C:19]([OH:21])=[O:20])=[O:12])=[C:8]([CH3:10])[N:9]=1)[C:2]([NH2:4])=[NH:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178433202HCID 178433202, compound

Product 1

HCID 178433201HCID 178433201, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

142 mg of tert-butyl {3-[(2-guanidino-4-methyl-thiazole-5-carbonyl)-amino]-phenoxy}-acetate is stirred in 1.1 ml of methylene chloride and 1.1 ml of trifluoroacetic acid (TFA) for 2 hrs. at RT. The reaction mixture is evaporated in a vacuum, the residue is taken up in water and the solution is evaporated to dryness. The solid is suspended in water, adjusted to pH 8 with 1N ammonia while stirring, filtered off under suction, washed with water and dried. There are obtained 101 mg of [3-[(2-guanidino-4-methyl-thiazole-5-carbonyl)-amino]-phenoxy]-acetic acid, m.p. 284° C., MS: 350 (M+H)+.

Workup

  1. customat RT
  2. customThe reaction mixture is evaporated in a vacuum
  3. customthe solution is evaporated to dryness
  4. filtrationfiltered off under suction
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-51ead022fbaf44de891b4b0d6a9829bd
Source dataset
uspto-grants-2001_10
Patent number
US06297266B1

Reaction notes

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