Triethylamine → HCID 86663416, compound

HRID 446494Notes

Reaction equation

HRID 446494 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:36])([F:35])[C:8]1[CH:9]=[C:10]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:11]([N:13]1[CH2:17][C@@:16]([CH2:25][CH2:26][OH:27])([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[O:15][CH2:14]1)=[O:12].C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][S:2]([O:27][CH2:26][CH2:25][C@:16]1([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[O:15][CH2:14][N:13]([C:11](=[O:12])[C:10]2[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=[C:8]([C:7]([F:35])([F:6])[F:36])[CH:9]=2)[CH2:17]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86663414HCID 86663414, compound

Product 1

HCID 86663416HCID 86663416, compoundYield 90.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (26 mL, 0.336 mol) was added dropwise to a solution of the compound (102.11 g, 0.226 mol) obtained in Example 1c, triethylamine (63 mL, 0.452 mol) and 4-(dimethylamino)pyridine (2.76 g, 0.0273 mol) in dichloromethane (1000 mL) under ice cooling, and the mixture was stirred under ice cooling for 1 hour. The reaction mixture was washed with water and saturated sodium chloride solution, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-n-hexane, 30%→50%) to give the title compound (108.21 g; yield, 90%) as a white solid.

Workup

  1. washThe reaction mixture was washed with water and saturated sodium chloride solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate-n-hexane, 30%→50%)

Sources & evidence

ORD record
ord-83c156e6cfc243309f68babe1d529af5
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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