Triethylamine → HCID 76812795, compound

HRID 1014921Notes

Reaction equation

HRID 1014921 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH:14]=[CH:15][CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH3:13])[CH:9]1[CH:14]=[CH:15][CH2:16][O:17][S:26]([CH3:25])(=[O:28])=[O:27])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66671642HCID 66671642, compound

Product 1

HCID 76812795HCID 76812795, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution containing 62 (6.0 g, 0.025 mol) in DCM (25 mL) at 0° C. was added Et3N (4.5 mL, 0.032 mol). After 5 min, a solution containing methanesulfonylchloride (2.33 mL, 0.03 mol) in DCM (5 mL) was added drop wise. After 2 h, TLC analysis revealed complete consumption of 62 [1:1 hexanes/EtOAc, Rf(63)=0.5, Rf(62)=0.4]. The reaction mixture was poured onto ice-water and extracted with DCM. The organic extracts were washed with water, brine, and dried over anhydrous Na2SO4, filtered, and concentrated to afford 7.05 g (89%) of crude 63 as a pale brown oil which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ5.8-5.5 (m, 2H), 4.69 (d. J=6.15 Hz, 2H), 3.85-3.3 (m, 3H), 3.0 (s, 3H), 2.0-1.9 (m, 1H), 1.55-1.30 (m, 1H), 1.40 (s, 9H), 1.0 (d, J=6.74 Hz, 3H) ppm.

Workup

  1. additionwas added drop wise
  2. waitAfter 2 h
  3. customconsumption of 62 [1:1 hexanes/EtOAc, Rf(63)=0.5, Rf(62)=0.4]
  4. additionThe reaction mixture was poured onto ice-water
  5. extractionextracted with DCM
  6. washThe organic extracts were washed with water, brine
  7. dry with materialdried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b3373af81bd74290977b3443957cc16b
Source dataset
uspto-grants-2011_07
Patent number
US07985735B2

Reaction notes

Loading…