Trifluoroacetic acid → HCID 67617792, compound

HRID 2396353Notes

Reaction equation

HRID 2396353 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 hoursand 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-fcfee77ec92c4a2786a317abc5f6b3ec
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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