Hydrochloric Acid → HCID 69456015, compound

HRID 1351973Notes

Reaction equation

HRID 1351973 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([NH:21][C:22](=O)[C@H:23]([OH:30])[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCCC1.CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([NH:21][CH2:22][C@@H:23]([C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[OH:30])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69456184HCID 69456184, compound

Product 1

HCID 69456015HCID 69456015, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (2R)-N-((1R)-2-(7-(benzyloxy)-1H-indol-3-yl)-1-methylethyl)-2-hydroxy-2-pyridin-3-ylacetamide (283 mg, 0.681 mmol) in tetrahydrofuran (15 mL) is added a 2M solution of boranedimethyl sulfide complex in tetrahydrofuran (2.04 mL, 4.09 mmol), and the mixture is refluxed for 3 hours. To the reaction solution is added a 10% hydrogen chloride solution in methanol (30 mL), and the mixture is stirred for 30 minutes. The solvent is evaporated, and the residue is separated into a saturated aqueous sodium hydrogen carbonate solution and chloroform. The organic layer is washed with a saturated brine, and dried over sodium sulfate. The solvent is distilled off, and the obtained crude product is purified by silica gel column chromatography (a saturated ammonia solution in chloroform-methanol=100:1) to give the title compound (184.8 mg, yield: 68%).

Workup

  1. temperaturethe mixture is refluxed for 3 hours
  2. customThe solvent is evaporated
  3. customthe residue is separated into a saturated aqueous sodium hydrogen carbonate solution and chloroform
  4. washThe organic layer is washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvent is distilled off
  7. customthe obtained crude product
  8. customis purified by silica gel column chromatography (a saturated ammonia solution in chloroform-methanol=100:1)

Sources & evidence

ORD record
ord-70e4ff26a7aa458eb27d811524b7ebbf
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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