Trifluoroacetic acid → HCID 11613999, compound

HRID 2301532Notes

Reaction equation

HRID 2301532 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]([OH:35])=[C:18]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])=[O:25])[CH:19]=[CH:20][C:21]=1[Cl:22])(=[O:15])=[O:14])=O)(C)(C)C.[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39]>>[F:36][C:37]([F:42])([F:41])[C:38]([OH:40])=[O:39].[NH2:8][CH2:9][CH2:10][CH2:11][NH:12][S:13]([C:16]1[C:17]([OH:35])=[C:18]([NH:23][C:24]([NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])=[O:25])[CH:19]=[CH:20][C:21]=1[Cl:22])(=[O:14])=[O:15]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11628346HCID 11628346, compound

Product 1

HCID 11613999HCID 11613999, compoundYield 68%

Procedure

A solution of N[3-[N″-[3-(tert-butoxycarbonylamino)propyl]aminosulfonyl]-4-chloro-2-hydroxyphenyl]-N′-(2,3-dichlorophenyl) urea (33 mg, 0.058 mmol) in 1 mL of trifluoroacetic acid was stirred at room temperature for 30 min. The solvent was concentrated. The residue was diluted with methanol, then concentrated. The process was repeated twice to give crude material. Recrystallization from methanol and water produced desired product (23 mg, 68%). EI-MS (m/z) 466.7, 468.8, 470.8 (M−).

Workup

  1. concentrationThe solvent was concentrated
  2. additionThe residue was diluted with methanol
  3. concentrationconcentrated
  4. customto give crude material
  5. customRecrystallization from methanol and water

Sources & evidence

ORD record
ord-9255e74c500642de98f81aa4a95132bd
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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