Ammonium Chloride → 2-(3-Amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester

HRID 1355252Notes

Reaction equation

HRID 1355252 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N+:21]([O-])=O)[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl-].[NH4+]>CO.O.[Zn]>[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[C:13]([NH2:21])[CH:12]=1)[CH2:5][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 120695073-Cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester

Product 1

HCID 544385412-(3-Amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl esterYield 108.5%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionic acid methyl ester (prepared as in Example 14, 1.50 g, 4.22 mmol) in methanol (30 mL) was treated with a solution of ammonium chloride (474 mg, 8.86 mmol) in water (3 mL). The reaction mixture was stirred at 25° C. for 5 min and then treated with zinc dust (2.70 g, 41.36 mmol). The reaction mixture was heated under reflux for 2 h. The reaction mixture was allowed to cool to 25° C. and then filtered through a pad of celite. The filtrate was concentrated in vacuo. The resulting orange oil was dissolved in ethyl acetate, dried over magnesium sulfate, filtrated, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 2/1 hexanes/ethyl acetate) afforded 2-(3-amino-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid methyl ester (1.49 g, 98%) as a white solid: mp 98–100° C.; EI-HRMS m/e calcd for C16H23NO4S (M+) 325.1348, found 325.1358.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool to 25° C.
  4. filtrationfiltered through a pad of celite
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionThe resulting orange oil was dissolved in ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4b917f1ebbd4b278f22158b4e711730
Source dataset
uspto-grants-2007_05
Patent number
US07223868B2

Reaction notes

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