Trifluoroacetic acid → HCID 67617792, compound

HRID 1488823Notes

Reaction equation

HRID 1488823 reaction equation
[CH2:1]([CH2:10][CH2:11][O:12][C:13]([CH2:15][NH:16][C:17]1[C:25]2[C:20](=[CH:21][C:22]([Cl:27])=[CH:23][C:24]=2[Cl:26])[N:19](C(OC(C)(C)C)=O)[C:18]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:14])[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH2:1]([CH2:10][CH2:11][O:12][C:13]([CH2:15][NH:16][C:17]1[C:25]2[C:20](=[CH:21][C:22]([Cl:27])=[CH:23][C:24]=2[Cl:26])[NH:19][C:18]=1[C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:14])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67618593HCID 67618593, compound

Product 1

HCID 67617792HCID 67617792, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve 3-[(phenacyl)carbethoxymethyl-amino]-2-carbethoxy-4,6-dichloro-1-tert-butyloxycarbonyl-indole (0.4 g, 0.71 mmol) in methylene chloride (6 mL) and add, by dropwise addition, trifluoroacetic acid (6 mL). Stir for 3.5 hours and pour slowly into saturated sodium hydrogen carbonate (100 mL). Extract with ethyl acetate and dry (MgSO4). Evaporate the solvent in vacuo and recrystallize the residue (ethyl acetate/hexane) to give the title compound (0.28 g, 85%); mp 139°-40° C.

Workup

  1. extractionExtract with ethyl acetate
  2. dry with materialdry (MgSO4)
  3. customEvaporate the solvent in vacuo
  4. customrecrystallize the residue (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-03aa336de0df454b87217b2350af554c
Source dataset
uspto-grants-1997_10
Patent number
US05675018

Reaction notes

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