Acetic Acid → 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylamino)-pyrazin-2-yl]-propionamide

HRID 719995Notes

Reaction equation

HRID 719995 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][CH2:35]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([NH:22][CH2:23][CH2:24][O:25][Si](CC)(CC)CC)=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(O)(=O)C>O1CCCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:12]([CH2:33][CH:34]2[CH2:35][CH2:36][CH2:37][CH2:38]2)[C:13]([NH:15][C:16]2[CH:21]=[N:20][C:19]([NH:22][CH2:23][CH2:24][OH:25])=[CH:18][N:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 674825802(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-triethylsilanyloxy-ethylamino)-pyrazin-2-yl]-propionamide

Product 1

HCID 104122722(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylamino)-pyrazin-2-yl]-propionamideYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-triethylsilanyloxy-ethylamino)-pyrazin-2-yl]-propionamide (100 mg, 0.17 mmol) in tetrahydrofuran (2 mL), water (0.5 mL), and acetic acid (2 mL) was stirred at 25° C. for 6 h. The reaction mixture was then diluted with water (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (10 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 12M, Silica, 2/3 hexanes/ethyl acetate to 100% ethyl acetate) afforded 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(2-hydroxy-ethylamino)-pyrazin-2-yl]-propionamide (69 mg, 86%) as a white foam: (ES)+-HRMS m/e calcd for C21H27ClN4O4S (M+H)+ 467.1515, found 467.1517.

Workup

  1. extractionextracted with ethyl acetate (3×20 mL)
  2. washThe combined organic layers were washed with a saturated aqueous sodium bicarbonate solution (10 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd723a9e3c6e4d938d07550f23bd102a
Source dataset
uspto-grants-2006_11
Patent number
US07132425B2

Reaction notes

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