Dichloromethane → HCID 21460764, compound

HRID 2396351Notes

Reaction equation

HRID 2396351 reaction equation
[CH2:1]([N:10]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=2)[N:13](C(OC(C)(C)C)=O)[C:12]1([C:29]([O:31][CH2:32][CH3:33])=[O:30])Cl)[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:54]>>[CH2:1]([N:10]([CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:11]1[C:19]2[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][C:18]=2[Cl:54])[NH:13][C:12]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:2]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)=[O:3]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21460794HCID 21460794, compound

Product 1

HCID 21460764HCID 21460764, compoundYield 59%

Procedure

Dissolve 3-[(phenacyl)benzylamino]-2-carbethoxy-2,6-dichloro-1-tert-butyloxycarbonyl-indole (0.68 g, 1.26 mmol) in methylene chloride (5 mL) and add, by dropwise addition, trifluoroacetic acid (5 mL). Stir for 4 hours then slowly add to saturated sodium hydrogen carbonate (100 mL). Extract into methylene chloride, dry (MgSO4) and evaporate the solvent in vacuo. Recrystallize (ethyl acetate/hexane) to give the title compound (0.34 g, 59%); mp 174°-5° C.

Workup

  1. extractionExtract into methylene chloride
  2. dry with materialdry (MgSO4)
  3. customevaporate the solvent in vacuo
  4. customRecrystallize (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5a74bf8f2686466293b1b9cffc4f7bb4
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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