Trifluoroacetic acid → 5-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dione

HRID 1592972Notes

Reaction equation

HRID 1592972 reaction equation
[O:1]=[C:2]1[NH:6][C:5](=[O:7])[CH:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][N:22](C)[C:23](=O)OC(C)(C)C)[CH:16]=3)=[CH:11][CH:10]=2)[S:3]1.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:23][NH:22][CH2:21][C:17]1[CH:16]=[C:15]([C:12]2[CH:11]=[CH:10][C:9]([CH2:8][CH:4]3[S:3][C:2](=[O:1])[NH:6][C:5]3=[O:7])=[CH:14][CH:13]=2)[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 10202718Tert-butyl [4'-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamate

Product 1

HCID 120854865-(3'-Methylaminomethylbiphenyl-4-ylmethyl)thiazolidine-2,4-dioneYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

18 g (42 mmol) of tert-butyl [4′-(2,4-dioxothiazolidin-5-ylmethyl)biphenyl-3-ylmethyl]methylcarbamate in 250 ml of dichloromethane are introduced into a round-bottomed flask and under a nitrogen stream, and 16 ml (208 mmol) of trifluoroacetic acid are added. The mixture is stirred at room temperature overnight and the reaction medium is hydrolysed with a saturated potassium carbonate solution. The mixture is extracted with dichloromethane, the organic phase decanted off, washed with water, dried over magnesium sulphate and evaporated off. The residue obtained is triturated in ethyl acetate and 14.4 g (78%) of the expected product are obtained.

Workup

  1. additionare added
  2. extractionThe mixture is extracted with dichloromethane
  3. customthe organic phase decanted off
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated off
  7. customThe residue obtained
  8. customis triturated in ethyl acetate

Sources & evidence

ORD record
ord-dce2f722e43a4984b51a0da1e0004c71
Source dataset
uspto-grants-2007_11
Patent number
US07294639B2

Reaction notes

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