Trifluoroacetic acid → HCID 9912131, compound

HRID 1280826Notes

Reaction equation

HRID 1280826 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[C:11]([NH:34][C:35]([NH2:37])=[O:36])=[C:12]([CH2:32][CH3:33])[N:13]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)(C)(C)C.FC(F)(F)C(O)=O>>[CH2:32]([C:12]1[N:13]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:14]2[C:10]([C:11]=1[NH:34][C:35]([NH2:37])=[O:36])=[C:9]([O:8][CH2:7][C:6]([OH:38])=[O:5])[CH:17]=[CH:16][CH:15]=2)[CH3:33]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53780023HCID 53780023, compound

Product 1

HCID 9912131HCID 9912131, compoundYield 56.1%

Procedure

[[2-Ethyl-1-(2-(4-fluorophenyl)-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid tert-butyl ester (0.4 g) was treated with 2 mL of trifluoroacetic acid at room temperature. After two hours the excess acid was removed under vacuum, 5 mL of 1N hydrochloric acid added, the mixture extracted with ethyl acetate, which was washed, dried, and concentrated. The residue was treated with 2 mL of 1 N hydrochloric acid and stirred for several hours. The resulting tan solid was isolated by filtration to afford 0.20 g of [[2-ethyl-1-(2-(4-fluorophenyl)-phenylmethyl)-3-ureido-1H-indol-4-yl]oxy]acetic acid. Mass spectrum: 461

Workup

  1. customAfter two hours the excess acid was removed under vacuum, 5 mL of 1N hydrochloric acid
  2. additionadded
  3. extractionthe mixture extracted with ethyl acetate, which
  4. washwas washed
  5. customdried
  6. concentrationconcentrated
  7. additionThe residue was treated with 2 mL of 1 N hydrochloric acid
  8. customThe resulting tan solid was isolated by filtration

Sources & evidence

ORD record
ord-b243643b6bf549509dd1fed73c0e4b62
Source dataset
uspto-grants-2002_09
Patent number
US06451839B1

Reaction notes

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