Triethylamine → HCID 57789220, compound

HRID 1625541Notes

Reaction equation

HRID 1625541 reaction equation
[CH3:1][N:2]([CH2:13][C:14]#[CH:15])[C@H:3]([CH3:12])[C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)O.C(N(CC)CC)C.S([Cl:27])(C)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Cl:27][C@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C@H:3]([N:2]([CH3:1])[CH2:13][C:14]#[CH:15])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 57789228HCID 57789228, compound

Product 1

HCID 57789220HCID 57789220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2b (120 mg, 0.54 mmol) and triethyl amine (1.0 mmol), in THF (2 ml) was stirred at room temperature for 30 min. To the stirred mixture mesylchloride (0.60 mmol) was added drop wise at −7° C. and the reaction mixture was stirred at room temperature for additional 30 min. Saturated Na2CO3 solution (1 mL) was added and stirred for 30 more min. The organic layer was partitioned between CH2Cl2 (15 ml) and water (10 ml). The organic phase was separated and washed with saturated NaHCO3 (10 ml) and brine (10 ml) and dried over MgSO4 and filtered. The solvent was removed under reduced pressure to obtain the crude product as light yellow oil. The crude product was purified by silica-gel column chromatography (hexane/ether 3:1).

Workup

  1. stirringstirred for 30 more min
  2. customThe organic layer was partitioned between CH2Cl2 (15 ml) and water (10 ml)
  3. customThe organic phase was separated
  4. washwashed with saturated NaHCO3 (10 ml) and brine (10 ml)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-215e99fe0b1548a09c2df18802ce22b8
Source dataset
uspto-grants-2014_07
Patent number
US08784775B2

Reaction notes

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