Benzoyl chloride → HCID 59850297, compound

HRID 1642647Notes

Reaction equation

HRID 1642647 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[S:18](=[O:20])(=[O:19])[NH:17][C:16](=[O:21])[CH2:15]2)=[C:10]([OH:22])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:15][C:16](=[O:21])[NH:17][S:18]2(=[O:20])=[O:19])=[C:10]([O:22][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 23665647Potassium tert-butoxideHCID 24895697HCID 24895697, compound

Product 1

HCID 59850297HCID 59850297, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-benzyl-2-hydroxyphenyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (45 mg, 0.141 mmol) in DMF (0.2 mL) is added KOtBu (1.0 M in THF, 0.17 mL, 0.17 mmol). After it is stirred at ambient temperature for 5 min., benzoyl chloride (35 mg, 0.254 mmol) is added. After it is stirred at ambient temperature for 10 min., the reaction is quenched with 1N HCl solution. The residue is then purified by prep. HPLC using CH3CN (0.1% TFA)/water (5-70%) to give the title compound: MS (M−H)−=421.

Workup

  1. stirringAfter it is stirred at ambient temperature for 10 min.
  2. customthe reaction is quenched with 1N HCl solution
  3. customThe residue is then purified by prep

Sources & evidence

ORD record
ord-906de45988364db09f1bce0f8b8c9968
Source dataset
uspto-grants-2012_02
Patent number
US08119666B2

Reaction notes

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