Trifluoroacetic acid → HCID 22053765, compound

HRID 1829615Notes

Reaction equation

HRID 1829615 reaction equation
C([O:5][C:6]([C:8]1[C:9]([CH3:28])=[C:10]([C:25]([OH:27])=[O:26])[S:11][C:12]=1[NH:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:15])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCOC(C)=O>[CH3:28][C:9]1[C:8]([C:6]([OH:7])=[O:5])=[C:12]([NH:13][C:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:15])[S:11][C:10]=1[C:25]([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21030700HCID 21030700, compound

Product 1

HCID 22053765HCID 22053765, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(7.1) To a stirring solution of 3-methyl-5-(3-octyl-ureido)-thiophene-2,4-dicarboxylic acid 4-tert-butyl ester (50.0 mg, 0.13 mmol) in CH2Cl2 (1 mL) was added TFA (1 mL). The reaction was stirred at RT for 2 h, and then solvent was removed under reduced pressure to give a solid. The product was dissolved in EtOAc, washed with sat. NaHCO3 (aq.), and brine. The organic layer was dried with MgSO4, filtered, and concentrated under reduced pressure to give 10.0 mg of a solid (22%): 1H NMR (CDCl3) δ 10.45 (bs, 1H), 6.27 (bs, 1H), 5.00 (bs, 1H), 3.50-3.20 (m, 2H), 2.37 (s, 3H), 1.70-1.40 (m, 2H), 1.26 (bs, 10H), 0.88 (t, 3H, J=6.2 Hz). MS (EI): 312.9 (m+—COOH).

Workup

  1. customsolvent was removed under reduced pressure
  2. customto give a solid
  3. washwashed with sat. NaHCO3 (aq.), and brine
  4. dry with materialThe organic layer was dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7352121835e74f9a896524deea2d6633
Source dataset
uspto-grants-2006_06
Patent number
US07064122B2

Reaction notes

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