Triethylamine → HCID 22959601, compound

HRID 1860172Notes

Reaction equation

HRID 1860172 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([OH:15])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[NH:30]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C>C1(C)C=CC=CC=1>[CH2:22]([C@@H:29]1[CH2:33][O:32][C:31](=[O:34])[N:30]1[C:13](=[O:15])[C@H:12]([C:4]1[CH:5]=[CH:6][C:7]([S:8]([CH3:11])(=[O:9])=[O:10])=[C:2]([Cl:1])[CH:3]=1)[CH2:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 120676542-(3-Chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

Product 1

HCID 22959601HCID 22959601, compoundYield 26.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 2-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared in Example 28, 6.1 g, 18.3 mmol), (R)-(+)-4-benzyl-2-oxazolidinone (2.83 g, 15.9 mmol), triethylamine (6.68 mL, 47.7 mmol), in toluene (50 mL) heated to 80° C. was treated with pivaloyl chloride (3.55 mL, 28.8 mmol) in toluene (10 mL). The resulting slurry was heated at 80° C. for 36 h. At this time, the reaction was cooled to 20° C. and concentrated in vacuo. The residue was diluted with ethyl acetate (150 mL) washed with a 1N aqueous hydrochloric acid solution (100 mL), a 10% aqueous sodium carbonate solution (100 mL), and a saturated aqueous sodium chloride solution (100 mL). The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 90/5/5 methylene chloride/hexanes/ethyl acetate) afforded 4(R)-benzyl-3-[2(S)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-oxazolidin-2-one (2.08 g, 23%) as a white foam: [α]23589=+10.4° (c=0.144, chloroform); FAB-HRMS m/e calcd for C25H2SClNO5S (M+H)+490.1455, found 490.1457 and 4(R)-benzyl-3-[2(R)-(3-chloro methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-oxazolidin-2-one (2.20 g, 25%) as a white foam: [α]23589=−93.9° (c=0.165, chloroform); FAB-HRMS m/e calcd for C25H28ClNO5S (M+H)+490.1455, found 490.1443.

Workup

  1. temperatureAt this time, the reaction was cooled to 20° C.
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with ethyl acetate (150 mL)
  4. washwashed with a 1N aqueous hydrochloric acid solution (100 mL)
  5. dry with materialThe organics were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e0c94f7486f4207934a6f437bd9024c
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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