HCID 67130404, compound → HCID 67130555, compound

HRID 2380970Notes

Reaction equation

HRID 2380970 reaction equation
C([O:5][C:6](=[O:31])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([S:22]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[C:25]1([S:22]([N:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)[C:10]2[CH:11]=[CH:12][C:7]([C:6]([OH:31])=[O:5])=[CH:8][CH:9]=2)(=[O:24])=[O:23])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

3

Reactant 1

HCID 67130404HCID 67130404, compound

Product 1

HCID 67130555HCID 67130555, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 4-[benzenesulfonyl-(4-chloro-benzyl)-amino]-benzoic acid tert-butyl ester (2.1 g, 4.4 mmol) in 10% trifluoroacetic acid/dichloromethane (50 mL) was stirred at room temperature for 16 hours. The reaction mixture was concentrated in vacuo and the residue partitioned between sodium hydrogen carbonate (saturated solution, 25 mL) and dichloromethane (20 mL). The aqueous layer was separated, acidified (pH 1) using 10% HCl (aq) and the resulting solution extracted with dichloromethane (3×75 mL). The organics were combined, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a white solid (1.1 g, 62% yield)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue partitioned between sodium hydrogen carbonate (saturated solution, 25 mL) and dichloromethane (20 mL)
  3. customThe aqueous layer was separated
  4. extractionthe resulting solution extracted with dichloromethane (3×75 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-917c4637c4eb4e0f902c87843aaf10da
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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