Triethylamine → HCID 86614642, compound

HRID 1445840Notes

Reaction equation

HRID 1445840 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27](=[O:29])[CH3:28])[CH:22]=3)=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14].C(N(CC)CC)C>ClCCl>[C:27]([C:23]1[CH:22]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:11]3[O:12][C:13]([CH3:14])=[C:9]([CH2:8][CH2:7][O:6][S:2]([CH3:1])(=[O:4])=[O:3])[N:10]=3)=[CH:20][CH:19]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68701677HCID 68701677, compound

Product 1

HCID 86614642HCID 86614642, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (0.110 g, 0.760 mmol) to a cool (0° C.) solution of 1-{4′-[4-(2-hydroxy-ethyl)-5-methyl-oxazol-2-yl]-biphenyl-3-yl}-ethanone (0.188 g, 0.584 mmol) and triethylamine (0.089 g, 0.88 mmol) in dichloromethane (5 mL). Warm the reaction mixture to room temperature and stir for 1 hour. Add dichloromethane and wash the crude organic layer with saturated sodium chloride solution. Dry the organic extracts over Na2SO4, filter, and concentrate to give crude methanesulfonic acid 2-[2-(3′-acetyl-biphenyl-4-yl)-5-methyl-oxazol-4-yl]-ethyl ester (0.256 g, >100%).

Workup

  1. washAdd dichloromethane and wash the crude organic layer with saturated sodium chloride solution
  2. dry with materialDry the organic extracts over Na2SO4
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-0c24e63526644238a60d132a6a30204d
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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