Triethylamine → HCID 57692826, compound

HRID 1470684Notes

Reaction equation

HRID 1470684 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C@@H:9]1[C@@H:13]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C@H:12]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[CH2:11][C@@H:10]1[OH:29].CCN(CC)CC.C([O-])(O)=O.[Na+]>ClCCl>[CH3:1][S:2]([O:6][CH2:7][CH2:8][C@H:9]1[C@@H:10]([O:29][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:11][C@@H:12]([O:22][CH:23]2[CH2:28][CH2:27][CH2:26][CH2:25][O:24]2)[C@@H:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 68931295HCID 68931295, compound

Product 1

HCID 57692826HCID 57692826, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MsCl (0.60 mL, 7.72 mmol) was added to an ice cold solution of 6-1 (447 mg, 1.31 mmol) and Et3N (1.3 mL, 9.33 mmol) in dichloromethane (5 mL). The reaction was allowed to warm to room temperature and after 3 h, saturated NaHCO3 solution was added. The resulting mixture was extracted with dichloromethane (3×) and the combined dichloromethane solution was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (Combiflash unit by Isco) gave the title compound (326 mg, 50%).

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane (3×)
  2. dry with materialthe combined dichloromethane solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customPurification of the residue by flash chromatography on silica gel (Combiflash unit by Isco)

Sources & evidence

ORD record
ord-d0717478ca804ce38c0c799e5aef9a45
Source dataset
uspto-grants-2015_04
Patent number
US09006464B2

Reaction notes

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