Trifluoroacetic acid → [5'-chloro-1-(5-chloro-2-fluorobenzyl)-2,2',5-trioxospiro[imidazolidine-4,3'-indol]-1'(2'H)-yl]acetic acid

HRID 883669Notes

Reaction equation

HRID 883669 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[C:6](=[O:19])[C:5]12[C:23](=[O:24])[N:22]([CH2:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:21](=[O:34])[NH:20]1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6](=[O:19])[C:5]12[C:23](=[O:24])[N:22]([CH2:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[F:33])[C:21](=[O:34])[NH:20]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58017116HCID 58017116, compound

Product 1

HCID 16093474[5'-chloro-1-(5-chloro-2-fluorobenzyl)-2,2',5-trioxospiro[imidazolidine-4,3'-indol]-1'(2'H)-yl]acetic acidYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An ice-cold solution of tert-butyl [5′-chloro-1-(5-chloro-2-fluorobenzyl)-2,2′,5-trioxospiro[imidazolidine-4,3′-indol]-1′(2′H)-yl]acetate (168.00 mg; 0.33 mmol) in DCM (4.00 ml) was treated with trifluoroacetic acid (1.00 ml). After stirring for 4 hours the reaction the solvents were evaporated. Toluene was added twice and evaporated to give the titla compound as a beige solid in 67.5% yield (96.1% purity by HPLC). MS (ESI+): 452.1; MS (ESI−): 454.4

Workup

  1. customthe reaction the solvents
  2. customwere evaporated
  3. additionToluene was added twice
  4. customevaporated

Sources & evidence

ORD record
ord-612eb6708a1b4d68a331e2bc690bebeb
Source dataset
uspto-grants-2012_08
Patent number
US08236963B2

Reaction notes

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