1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-[5-(2,4-Dimethoxy-benzyl)-1,1,4-trioxo1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 2-ethyl-butyl ester

HRID 1591984Notes

Reaction equation

HRID 1591984 reaction equation
C1CCN2C(=NCCC2)CC1.[CH2:12]([CH:14]([CH2:27][CH3:28])[CH2:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24]Br)=[CH:20][CH:19]=1)[CH3:13].[CH3:29][O:30][C:31]1[CH:45]=[C:44]([O:46][CH3:47])[CH:43]=[CH:42][C:32]=1[CH2:33][N:34]1[C:38](=[O:39])[CH2:37][NH:36][S:35]1(=[O:41])=[O:40]>C(Cl)Cl>[CH2:12]([CH:14]([CH2:27][CH3:28])[CH2:15][O:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:36]2[CH2:37][C:38](=[O:39])[N:34]([CH2:33][C:32]3[CH:42]=[CH:43][C:44]([O:46][CH3:47])=[CH:45][C:31]=3[O:30][CH3:29])[S:35]2(=[O:40])=[O:41])=[CH:20][CH:19]=1)[CH3:13]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 66751042HCID 66751042, compoundHCID 671383384-Bromomethyl-benzoic acid 2-ethyl-butyl ester

Product 1

HCID 671388714-[5-(2,4-Dimethoxy-benzyl)-1,1,4-trioxo1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 2-ethyl-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DBU (127 mg, 0.836 mmol) is added slowly to a suspension of the title B compound, 4-bromomethyl-benzoic acid 2-ethyl-butyl ester (250 mg, 0.836 mmol) and the title B compound in Example 9, 2-(2,4-dimethoxybenzyl)-1,1-dioxo-1,2,5-thiadiazolidin-3-one (240 mg, 0.836 mmol) in 10 mL of CH2Cl2 at RT. The resulting solution is stirred at RT overnight. The solvent is evaporated under reduced pressure and the residue is chromatographed on silica gel with EtOAc/hexane (gradient 60-40) to afford 4-[5-(2,4-dimethoxy-benzyl)-1,1,4-trioxo1,2,5-thiadiazolidin-2-ylmethyl]-benzoic acid 2-ethyl-butyl ester as a white solid.

Workup

  1. customat RT
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is chromatographed on silica gel with EtOAc/hexane (gradient 60-40)

Sources & evidence

ORD record
ord-d799ee9bf1804c63b171bf3f4eeafaae
Source dataset
uspto-grants-2007_11
Patent number
US07291635B2

Reaction notes

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