Trifluoroacetic acid → HCID 67617792, compound

HRID 2082515Notes

Reaction equation

HRID 2082515 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-2f139cb61acb413aa215118e3c41749c
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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