Acetic-formic anhydride → HCID 22627261, compound

HRID 1108739Notes

Reaction equation

HRID 1108739 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[C:7]([CH2:19][CH2:20][CH3:21])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:4][CH:3]=1.[CH:27](OC(=O)C)=[O:28]>ClCCl>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([NH:1][CH:27]=[O:28])[CH:10]=2)[C:6]([C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[C:7]1[CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 22627183HCID 22627183, compound

Product 1

HCID 22627261HCID 22627261, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-amino-1-(2-chlorobenzyl)-3-isobutyryl-2-propylindole (147 mg) in dichloromethane (2 ml) was added acetic formic anhydride (0.5 ml) at 0° C. The reaction mixture was stirred at 0° C. for 10 minutes, then diluted with dichloromethane. The organic phase was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2) to give crystals which were recrystallized from a mixture of ethyl acetate and hexane to give 1-(2-chlorobenzyl)-6-formamido-3-isobutyryl-2-propylindole (85 mg) as colorless crystals.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:2)
  5. customto give crystals which
  6. customwere recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-97423677a5af44408713fc2df094c8d6
Source dataset
uspto-grants-2000_05
Patent number
US06069156

Reaction notes

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