Diisopropylethylamine → HCID 59336768, compound

HRID 12018Notes

Reaction equation

HRID 12018 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@H:13]([OH:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C>CS(C)=O>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:13](=[O:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 68583088HCID 68583088, compound

Product 1

HCID 59336768HCID 59336768, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Pyridine-SO3 complex (285 mg, 1.79 mmol) is added to a solution of the compound of Example 68A (50 mg, 0.18 mmol) and N,N-diisopropylethylamine (310 μl, 1.79 mmol) in 2 ml of DMSO at 10° C. with and the mixture is slowly warmed to RT. After 2 h, 50 ml of ice/water are added to the reaction mixture. The mixture is extracted four times with diethyl ether. The combined organic phases are washed three times with a 10% citric acid solution, then three times with water and twice with a satd. sodium chloride solution, dried over magnesium sulfate and concentrated at 20° C. on a Rotavapor. The crude product (30 mg, 60% of th.) is reacted further without additional purification.

Workup

  1. extractionThe mixture is extracted four times with diethyl ether
  2. washThe combined organic phases are washed three times with a 10% citric acid solution
  3. dry with materialsodium chloride solution, dried over magnesium sulfate
  4. concentrationconcentrated at 20° C. on a Rotavapor
  5. customThe crude product (30 mg, 60% of th.) is reacted further without additional purification

Sources & evidence

ORD record
ord-9eb46e7b49624619b17b506a64b86825
Source dataset
uspto-grants-2010_06
Patent number
US07727956B2

Reaction notes

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