Triethylamine → HCID 22857728, compound

HRID 2259512Notes

Reaction equation

HRID 2259512 reaction equation
CS(Cl)(=O)=O.C([N:8]([CH2:11][CH3:12])CC)C.[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][C@H:22]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][O:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)[CH:31]=1)[O:23][CH2:24][C:25]1(CO)[CH2:27][CH2:26]1.C([O-])(O)=O.[Na+].S([O-])(=O)(=O)C.[C-]#N.[Na+]>C(Cl)Cl.CS(C)=O.O>[Br:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][CH2:21][C@H:22]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][O:37][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)[CH:31]=1)[O:23][CH2:24][C:25]1([CH2:12][C:11]#[N:8])[CH2:27][CH2:26]1

Participants

10

Reactant 6

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium Bicarbonate2×HCID 22857729HCID 22857729, compound

Product 1

HCID 22857728HCID 22857728, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (2.90 mL, 37.5 mmol) and triethylamine (6.50 mL, 46.6 mmol) were added to a solution of the alcohol of Step 5 (15.30 g, 31.3 mmol) in 200 mL of CH2Cl2 at -40° C. and the solution was stirred at -40° C. for 30 min and at 0° C. for 1 hr. Aq. saturated NaHCO3 was then added and the mesylate was extracted in CH2C12, dried over Na2SO4, concentrated, and stripped twice with toluene. To a solution of this mesylate in 240 mL of anhydrous dimethylsulfoxide was added NaCN (7.69, 157 mmol) and the mixture was stirred at room temperature overnight. Water (1 L) was then added, followed by 250 mL of saturated NaHCO3 and the product was extracted in ether, washed with brine, dried over Na2SO4, and purified by flash chromatography on silica with EtOAc:toluene 5:95; yield: 13.43 g (86%).

Workup

  1. extractionthe mesylate was extracted in CH2C12
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. stirringthe mixture was stirred at room temperature overnight
  5. extractionthe product was extracted in ether
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. custompurified by flash chromatography on silica with EtOAc:toluene 5:95

Sources & evidence

ORD record
ord-7adebfc3adb74de3a7b593cb5f845785
Source dataset
uspto-grants-1995_12
Patent number
US05472964

Reaction notes

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