Thionyl Chloride → HCID 22714163, compound

HRID 352233Notes

Reaction equation

HRID 352233 reaction equation
[C:1]([NH:9][CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([N:17]2[C:26]3[CH:25]=[CH:24][CH:23]=[C:22]([C:27](O)=[O:28])[C:21]=3[C:20]3=[N:30][O:31][C:32]([CH3:33])=[C:19]3[C:18]2=[O:34])[CH2:12]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[BH4-].[Na+]>C1(C)C=CC=CC=1.C1COCC1.CO.CCOC(C)=O>[OH:28][CH2:27][C:22]1[C:21]2[C:20]3[C:19](=[C:32]([CH3:33])[O:31][N:30]=3)[C:18](=[O:34])[N:17]([CH:13]3[CH2:14][CH2:15][CH2:16][CH:11]([CH2:10][NH:9][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH2:12]3)[C:26]=2[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 3

HCID 24386Thionyl ChlorideHCID 4311764Sodium borohydrideHCID 22714071HCID 22714071, compound

Product 1

HCID 22714163HCID 22714163, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 598 (0.01 g, 0.022 mmol) in toluene (0.4 ml) under N2 was added thionyl chloride (0.1 ml) and heated at reflux for 3 h. The solution was concentrated using toluene to azeotrope and the residue was dissolved in dichloromethane (0.5 ml). To this solution was added NaBH4 (0.008 g, 0.22 mmol) in THF (0.5 ml) and stirred overnight. The mixture was diluted with MeOH (1 ml) and EtOAc, washed (0.1 N NaOH, H2O, and brine), dried (MgSO4), filtered, and concentrated to give the title compound (0.005 g, 53%) without further purification.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. concentrationThe solution was concentrated
  4. dissolutionthe residue was dissolved in dichloromethane (0.5 ml)
  5. washwashed (0.1 N NaOH, H2O, and brine)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f2ce0d0eb81e4b639a23aae1cae4a710
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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