Triethylamine → HCID 131728659, compound

HRID 1363329Notes

Reaction equation

HRID 1363329 reaction equation
C(N(CC)CC)C.[CH3:8][N:9]1[CH2:14][CH2:13][C@@H:12]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=2[O:25][CH3:26])[C@H:11]([OH:27])[CH2:10]1.CS(Cl)(=O)=O.C([O-])(O)=O.[Na+].[C:38]([O-])(=[O:40])[CH3:39].[Na+]>C(Cl)Cl.C(O)(C)C>[CH3:8][N:9]1[CH2:14][CH2:13][C@@H:12]([C:15]2[C:16]([O:25][CH3:26])=[CH:17][C:18]([O:23][CH3:24])=[CH:19][C:20]=2[O:21][CH3:22])[C@@H:10]1[CH2:11][O:27][C:38](=[O:40])[CH3:39]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 517045Sodium AcetateHCID 68880556HCID 68880556, compound

Product 1

HCID 131728659HCID 131728659, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Distilled triethyl amine (344 mL, 2.49 mol) was added slowly to a solution of compound of example 2 (350 g, 1.25 mol) in dry CH2Cl2 (2.5 L). To the reaction mixture methanesulfonyl chloride (122 mL, 171.1 g, 1.49 mol) was added with stirring, at 0° C., under an atmosphere of N2 and over a period of 20 min. The reaction mixture was further stirred for 1 h at 0° C. It was poured over saturated aqueous NaHCO3 solution (1.5 L). The organic layer was separated, washed with brine, dried (anhydrousNa2SO4) and concentrated to obtained a residue. This was dissolved in distilled isopropyl alcohol (1.5 L), anhydrous sodium acetate (408 g, 4.97 mmol) was added and the reaction mixture was refluxed for 1 h. It was cooled to room temperature. Sodium acetate was filtered off and washed with CHCl3. The filtrate was concentrated to obtain the title compound, which was purified using a silica gel column and 60% EtOAc+petroleum ether 60-80° C. as eluant.

Workup

  1. stirringThe reaction mixture was further stirred for 1 h at 0° C
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried (anhydrousNa2SO4)
  5. concentrationconcentrated
  6. customto obtained a residue
  7. temperaturethe reaction mixture was refluxed for 1 h
  8. temperatureIt was cooled to room temperature
  9. filtrationSodium acetate was filtered off
  10. washwashed with CHCl3
  11. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9bedf4b9cd93464eaa8a8170faa25565
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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