Trifluoroacetic acid → HCID 58531469, compound

HRID 1889626Notes

Reaction equation

HRID 1889626 reaction equation
[Cl:1][C:2]1[C:3]([OH:45])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:23]=[C:24]([CH:34]=[C:35]([O:37][C:38]3[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=3)[CH:36]=2)[CH2:25][NH:26]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:26][CH2:25][C:24]1[CH:23]=[C:22]([CH:36]=[C:35]([O:37][C:38]2[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=2)[CH:34]=1)[CH2:21][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[S:9]([C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[OH:45])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58531386HCID 58531386, compound

Product 1

HCID 58531469HCID 58531469, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-5-(4-fluorophenoxy)benzylcarbamate (0.65 g, 0.96 mmol) in CH2Cl2 (8 mL) was added TFA (1.10 mL, 14.4 mmol). The reaction mixture was stirred at rt. for 3 h. The reaction mixture was concentrated and to the residue was added saturated NaHCO3 solution and ethyl acetate. The organic layer was washed with brine twice, dried over MgSO4, and concentrated in vacuo to give white solid (0.53 g, 96%). 1H NMR (CD3OD): δ 7.49 (d, J=2.8 Hz, 1H), 7.35 (d, J=2.8 Hz, 1H), 7.21-7.09 (m, 4H), 6.99-6.90 (m, 5H), 6.85 (s, 1H), 6.64 (s, 1H), 4.48 (s, 2H), 4.40 (s, 2H), 3.93 (s, 2H); MS (ESI): (M+H)+=579.0.

Workup

  1. concentrationThe reaction mixture was concentrated and to the residue
  2. additionwas added saturated NaHCO3 solution and ethyl acetate
  3. washThe organic layer was washed with brine twice
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3931aac38ab84055ab122b7e3e78451c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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