Triethylamine → HCID 18920522, compound

HRID 862795Notes

Reaction equation

HRID 862795 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19]O.C(N(CC)CC)C.[S:42](Cl)([CH3:45])(=[O:44])=[O:43]>C(Cl)Cl>[CH3:45][S:42]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:16][CH2:17][CH2:18][CH2:19][S:42]([CH3:45])(=[O:44])=[O:43])(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18920510HCID 18920510, compound

Product 1

HCID 18920522HCID 18920522, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

Cool to 0° C. a mixture containing 3.0 gm of the product of Step F, 3.3 ml of triethylamine and 70 ml of CH2Cl2. In a dropwise fashion add 1.22 ml of mesylchloride in 10 ml of CH2Cl2, and stir the resulting mixture at 0° C. for 11/2 hours. Pour the mixture into 100 ml of CH2Cl2, wash with 200 ml of 1N AcOH, 100 ml of water, 100 ml of sat'd sodium bicarbonate, dry over MgSO4 and remove the solvent in vacuo. Flash chromatograph the residue, eluting from silica gel with 60% EtOAc/hexane to obtain 3.5 gm of the desired product. Rf is 0.39.

Workup

  1. washwash with 200 ml of 1N AcOH, 100 ml of water, 100 ml of sat'd sodium bicarbonate
  2. dry with materialdry over MgSO4
  3. customremove the solvent in vacuo
  4. washFlash chromatograph the residue, eluting from silica gel with 60% EtOAc/hexane

Sources & evidence

ORD record
ord-097ef8f5ead04015ab6f2f04ffef4bc9
Source dataset
uspto-grants-1998_02
Patent number
US05719193

Reaction notes

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