Chloroform → HCID 86743260, compound

HRID 232123Notes

Reaction equation

HRID 232123 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N-:4][N:3]=1.[CH2:8]([O:15][C:16]([NH:18][C@@H:19]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:20]([OH:24])[C:21]([OH:23])=[O:22])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[O:29]1[CH:34]=[CH:33][CH2:32][CH2:31][CH2:30]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>ClCCl>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N-:4][N:3]=1.[CH2:8]([O:15][C:16]([NH:18][C@@H:19]([CH2:25][CH:26]([CH3:28])[CH3:27])[CH:20]([O:24][CH:30]1[CH2:31][CH2:32][CH2:33][CH2:34][O:29]1)[C:21]([OH:23])=[O:22])=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 86743261HCID 86743261, compound

Product 1

HCID 86743260HCID 86743260, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

162 mg of (2RS,3S)-3-benzyloxycarbonylamino-2-hydroxy-5-methylhexanoic acid 3,5-dimethylpyrazolide was dissolved in 1 ml of dry dichloromethane, and 102 μl of dihydropyran and 0.8 mg of p-toluenesulfonic acid monohydrate were added thereto. The mixture was stirred at room temperature for 1.5 hours. Then, 10 ml of chloroform was added to the mixture, and the mixture was washed with a 4% sodium hydrogencarbonate and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain 207 mg of (2RS,3S)-3-benzyloxycarbonylamino-2-(2-tetrahydropyranyloxy)-5-methylhexanoic acid 3,5-dimethylpyrazolide as a colorless oily substance.

Workup

  1. washthe mixture was washed with a 4% sodium hydrogencarbonate
  2. dry with materiala saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  3. distillationThen, the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-e32e2314467f4905b78dbc8b62fadbbb
Source dataset
uspto-grants-1989_07
Patent number
US04851387

Reaction notes

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