Acetone → HCID 10050270, compound

HRID 719973Notes

Reaction equation

HRID 719973 reaction equation
C[N+]1([O-])CC[O:5]CC1.O.[Cl:10][C:11]1[CH:12]=[C:13]([C@@H:21]([CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:22]([NH:24][C:25]2[CH:30]=[N:29]C(C=C)=[CH:27][N:26]=2)=[O:23])[CH:14]=[CH:15][C:16]=1[S:17]([CH3:20])(=[O:19])=[O:18].[CH3:39][C:40]([CH3:42])=[O:41]>O1CCCC1.[Os](=O)(=O)(=O)=O.C1(C)C=CC=CC=1>[Cl:10][C:11]1[CH:12]=[C:13]([C@@H:21]([CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:22]([NH:24][C:25]2[CH:30]=[N:29][C:39]([CH:40]([OH:41])[CH2:42][OH:5])=[CH:27][N:26]=2)=[O:23])[CH:14]=[CH:15][C:16]=1[S:17]([CH3:20])(=[O:19])=[O:18]

Participants

8

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 82029Methyl morpholine oxideHCID 674826192(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-vinyl-pyrazin-2-yl)-propionamide

Product 1

HCID 10050270HCID 10050270, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneCatalystHCID 8028TetrahydrofuranCatalystHCID 30318Osmium TetroxideCatalyst

Conditions

Temperature
25 °C

Procedure

A solution of N-methyl morpholine oxide (27 mg, 0.23 mmol) and a 0.2M solution of osmium tetroxide in toluene (5 μL, 0.001 mmol) in acetone (0.5 mL) and water (0.5 mL) was treated with 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-(5-vinyl-pyrazin-2-yl)-propionamide (prepared as in Example 54, 50 mg, 0.115 mmol). Two drops of tetrahydrofuran were added to fully dissolve the substrate, and the resulting mixture was stirred at 25° C. overnight. The reaction mixture was concentrated in vacuo, and the residue was treated with water (10 mL) and methylene chloride (25 mL). The organic phase was washed with a 1 N aqueous hydrochloric acid solution (10 mL), and each aqueous phase was extracted with a small portion of methylene chloride. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(1,2-dihydroxy-ethyl)-pyrazin-2-yl]-propionamide (48 mg) as a colorless foam: (ES)+-HRMS m/e calcd for C21H26N3O5S (M+H)+ 468.1355, found 468.1357.

Workup

  1. dissolutionto fully dissolve the substrate
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additionthe residue was treated with water (10 mL) and methylene chloride (25 mL)
  4. washThe organic phase was washed with a 1 N aqueous hydrochloric acid solution (10 mL)
  5. extractioneach aqueous phase was extracted with a small portion of methylene chloride
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f7d165b633a14d9281d56633f1fdc2b4
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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