Triethylamine → HCID 131728659, compound

HRID 1363330Notes

Reaction equation

HRID 1363330 reaction equation
CS(Cl)(=O)=O.[CH3:6][N:7]1[CH2:12][CH2:11][C@@H:10]([C:13]2[C:18]([O:19][CH3:20])=[CH:17][C:16]([O:21][CH3:22])=[CH:15][C:14]=2[O:23][CH3:24])[C@H:9]([OH:25])[CH2:8]1.C(N(CC)CC)C.[C:33]([O-])(=[O:35])[CH3:34].[Na+]>C1COCC1.CC(O)C.CCOC(C)=O.O>[CH3:6][N:7]1[CH2:12][CH2:11][C@@H:10]([C:13]2[C:14]([O:23][CH3:24])=[CH:15][C:16]([O:21][CH3:22])=[CH:17][C:18]=2[O:19][CH3:20])[C@@H:8]1[CH2:9][O:25][C:33](=[O:35])[CH3:34]

Participants

9

Reactant 4

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

Product 1

HCID 131728659HCID 131728659, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (44.8 g, 0.4 mol) was added dropwise to a cooled and stirred solution of compound of example 2 (100 g, 0.35 mol) and triethylamine (71.88 g, 0.7 mol) in dry THF (1.0 L). The reaction mixture was further stirred for 45 min. at 0° C. The precipitate of triethylamine HCl was filtered and washed with dry THF (2×100 mL). The filtrate was added dropwise to a refluxing suspension of sodium acetate (115 g, 1.42 mol) in 2-propanol (1.0 L). The reaction mixture was refluxed for a further 15 min., diluted with EtOAc (1.0 L) and salts were filtered. The mixture of salts was washed with EtOAc (2×100 mL). The combined filtrate was concentrated to give a gum. Water (50 mL) was added to the gum with stirring to obtain a solid which was filtered and dried to yield the title compound.

Workup

  1. temperaturea cooled
  2. filtrationThe precipitate of triethylamine HCl was filtered
  3. washwashed with dry THF (2×100 mL)
  4. temperatureThe reaction mixture was refluxed for a further 15 min.
  5. filtrationwere filtered
  6. additionThe mixture of salts
  7. washwas washed with EtOAc (2×100 mL)
  8. concentrationThe combined filtrate was concentrated
  9. customto give a gum
  10. stirringwith stirring
  11. customto obtain a solid which
  12. filtrationwas filtered
  13. customdried

Sources & evidence

ORD record
ord-bf481c49fe3e40ceb8595216d2504c40
Source dataset
uspto-grants-2011_02
Patent number
US07884127B2

Reaction notes

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