Triethylamine → HCID 70896830, compound

HRID 638835Notes

Reaction equation

HRID 638835 reaction equation
C(N(CC)CC)C.CS(Cl)(=O)=O.C([O:17][C:18]([NH:20][C@@H:21]([CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C@H:22]([OH:32])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=O)(C)(C)C.S([O-])(=O)(=O)C>ClCCCl.ClCCl.C(OCC)C>[CH2:33]([C@H:21]1[C@H:22](/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])[O:32][C:18](=[O:17])[NH:20]1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 70896807HCID 70896807, compound

Product 1

HCID 70896830HCID 70896830, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (2.9 mL, 20.7 mmol) and methanesulfonyl chloride (0.8 mL, 10.3 mmol) are added in the stated order to a solution of the allylic alcohol obtained in example (4) 1.b) (2.6 g, 6.9 mmol) in 1,2 dichloroethane (50 mL), cooled to 0° C. The reaction is monitored by thin layer chromatography (diethyl ether). The mixture is stirred at 0° C. until mesylate formation is complete, then maintained at room temperature until the product has completely formed. The solution is diluted with dichloromethane (50 mL) and washed with cold water, a 10% aqueous solution of cold hydrochloric acid, a saturated NaHCO3 solution, a saturated NaCl solution then dried over anhydrous Na2SO4. The solvent is removed under reduced pressure and the product purified by flash chromatography on a silica gel column using diethyl ether as eluant. 1.54 g (74%) of a white solid are obtained.

Workup

  1. temperaturemaintained at room temperature until the product
  2. customhas completely formed
  3. washwashed with cold water
  4. dry with materiala 10% aqueous solution of cold hydrochloric acid, a saturated NaHCO3 solution, a saturated NaCl solution then dried over anhydrous Na2SO4
  5. customThe solvent is removed under reduced pressure
  6. customthe product purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-e085c6f3ff2e412b9fa54dc657bef592
Source dataset
uspto-grants-2010_04
Patent number
US07691818B2

Reaction notes

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