Trifluoroacetic acid → HCID 58531583, compound

HRID 1889629Notes

Reaction equation

HRID 1889629 reaction equation
[Cl:1][C:2]1[C:3]([OH:40])=[C:4]([S:9]([N:12]([CH2:24][C:25]2[CH:26]=[C:27]([CH:37]=[CH:38][CH:39]=2)[CH2:28][NH:29]C(=O)OC(C)(C)C)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[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>[NH2:29][CH2:28][C:27]1[CH:26]=[C:25]([CH:39]=[CH:38][CH:37]=1)[CH2:24][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]([F:21])([F:23])[F:22])=[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:40])(=[O:10])=[O:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66616642HCID 66616642, compound

Product 1

HCID 58531583HCID 58531583, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-((3,5-dichloro-2-hydroxy-N-(4-(trifluoromethyl)benzyl)phenylsulfonamido)methyl)benzylcarbamate (0.4 g, 0.65 mmol) in CH2Cl2 (10 mL) was added TFA (1.49 mL, 19.4 mmol). The resulting mixture was stirred at rt for 16 h. The mixture was concentrated, and the residue was partitioned between saturated NaHCO3 and ethyl acetate. The organic layer was washed with brine twice, dried over MgSO4, and concentrated in vacuo to give a light yellow solid (0.32 g, 86%). 1H NMR (DMF-d7): δ 7.52 (m, 2H), 7.50 (m, 4H), 7.48 (m, 2H), 7.2-7.0 (m, 2H), 4.75 (s, 2H), 4.51 (s, 2H), 4.25 (m, 2H); MS (ESI): (M+H)+=519.11.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between saturated NaHCO3 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-4a940e56a4904326ad866a0d60e4e415
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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