Trifluoroacetic acid → HCID 86588218, compound

HRID 1814316Notes

Reaction equation

HRID 1814316 reaction equation
C([O:5][C:6](=[O:39])[CH2:7][CH:8]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH3:25])=[S:23])=[CH:17][C:16]=1[O:26][CH2:27][CH2:28][C:29]1[CH:38]=[CH:37][CH:36]=[C:35]2[C:30]=1[CH:31]=[CH:32][CH:33]=[N:34]2)(=[O:14])=[O:13])[CH:9]=[O:10])(C)(C)C.[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41]>C(Cl)Cl>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[CH3:25][NH:24][C:22](=[S:23])[NH:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][CH:8]([CH:9]=[O:10])[CH2:7][C:6]([OH:39])=[O:5])(=[O:13])=[O:14])=[C:16]([O:26][CH2:27][CH2:28][C:29]2[CH:38]=[CH:37][CH:36]=[C:35]3[C:30]=2[CH:31]=[CH:32][CH:33]=[N:34]3)[CH:17]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86588216HCID 86588216, compound

Product 1

HCID 86588218HCID 86588218, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.084 g (0.147 mmol) 3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid tert-butyl ester and 20 mL (3:1 CH2Cl2:TFA) was stirred 2 h at room temperature. TLC analysis indicated starting material consumed. The solvent was removed under reduced pressure. To the residue was added 25 mL CH2Cl2 and the solvent removed under reduced pressure. The residue was triturated with 15 mL ether and the solid was filtered, washed with ether and dried at 40° C. 36 h to give 0.087 g (94%) of 3-[4-(3-methyl-thioureido)-2-(2-quinolin-5-yl-ethoxy)-benzenesulfonylamino]-4-oxo-butyric acid trifluoroacetate salt as a beige solid. MS (APCI) m/z 517 (M+1).

Workup

  1. customconsumed
  2. customThe solvent was removed under reduced pressure
  3. additionTo the residue was added 25 mL CH2Cl2
  4. customthe solvent removed under reduced pressure
  5. customThe residue was triturated with 15 mL ether
  6. filtrationthe solid was filtered
  7. washwashed with ether
  8. customdried at 40° C

Sources & evidence

ORD record
ord-f15a2d20a98f48d596a0bb4bd86b35f4
Source dataset
uspto-grants-2005_04
Patent number
US06875765B2

Reaction notes

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