HCID 21098845, compound → HCID 69458821, compound

HRID 1351951Notes

Reaction equation

HRID 1351951 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C@@H:7]([O:26][Si](CC)(CC)CC)[CH2:8][NH:9][C@H:10]([CH3:25])[CH2:11][C:12]2[C:20]3[C:15](=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)[CH:2]=1>FC(F)(F)C(O)=O>[OH:26][C@H:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[CH2:8][NH:9][C@H:10]([CH3:25])[CH2:11][C:12]1[C:20]2[C:15](=[C:16]([C:21]([O:23][CH3:24])=[O:22])[CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1

Participants

3

Reactant 1

HCID 21098845HCID 21098845, compound

Product 1

HCID 69458821HCID 69458821, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

methyl 3-[(2R)-2-(2-pyridin-3-yl-(2R)-2-(triethylsilyloxy)ethyl-amino)propyl]-1H-indole-7-carboxylate (0.72 g, 1.54 mmol) is dissolved in trifluoroacetic acid (20 mL), and the mixture is stirred at room temperature for one day. After concentrated, to the residue is added ethyl acetate, and the mixture is washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, dried over sodium sulfate, and concentrated. The residue is purified by silica gel column chromatography (methanol/chloroform=1/100→1/3) to give the desired methyl 3-[(2R)-2-((2R)-2-hydroxy-2-pyridin-3-ylethylamino)-propyl]-1H-indole-7-carboxylate (440 mg, yield: 81%).

Workup

  1. concentrationAfter concentrated, to the residue
  2. additionis added ethyl acetate
  3. washthe mixture is washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated brine, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel column chromatography (methanol/chloroform=1/100→1/3)

Sources & evidence

ORD record
ord-663a42165c8f422e817995de91c60bcf
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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