Trifluoroacetic acid → HCID 18976183, compound

HRID 2393596Notes

Reaction equation

HRID 2393596 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([CH2:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])([NH:25][C:26](=[O:35])[C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=2)[C:17]1=[O:43])=[O:14])(C)(C)C>C(Cl)Cl>[Cl:34][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[Cl:33])[C:26]([NH:25][C:18]1([CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:16]([CH2:15][C:13]([OH:14])=[O:12])[C:17]1=[O:43])=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18976184HCID 18976184, compound

Product 1

HCID 18976183HCID 18976183, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5 ml of trifluoroacetic acid was added to a solution of 700 mg of ethyl 3-[1-(t-butoxycarbonylmethyl)-3-(3,4-dichlorobenzoylamino)-2,3-dihydro-2-oxo-1H-indol-3-yl]propionate in methylene chloride (20 ml). The mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated to dryness under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to afford 651 mg of 2-[3-(3,4-dichlorobenzoylamino)-2,3-dihydro-3-(2-ethoxycarbonylethyl)-2-oxo-1H-indol-1-yl]acetic acid as colorless prism crystals. Melting point: 219° to 220° C., IR (Nujol) (cm-1): 3280, 1735, 1720, 1705, 1670, 1610, FAB-MS (m/z): 481 & 479 (MH+).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-4d82d0eaeea9427aa7ff03408cd3e9ca
Source dataset
uspto-grants-1998_09
Patent number
US05807883

Reaction notes

Loading…