Ammonium Hydroxide → 3-cyclopentyl-2-(3-hydroxy-phenyl)-N-thiazol-2-yl-propionamide

HRID 398623Notes

Reaction equation

HRID 398623 reaction equation
B(Br)(Br)Br.[CH:5]1([CH2:10][CH:11]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26]C)[CH:21]=2)[C:12]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:13])[CH2:9][CH2:8][CH2:7][CH2:6]1.[OH-].[NH4+]>C(Cl)Cl>[CH:5]1([CH2:10][CH:11]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([OH:26])[CH:21]=2)[C:12]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:13])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 223152813-cyclopentyl-2-(3-methoxy-phenyl)-N-thiazol-2-yl-propionamide

Product 1

HCID 223151133-cyclopentyl-2-(3-hydroxy-phenyl)-N-thiazol-2-yl-propionamideYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A 1.0M solution of boron tribromide in methylene chloride (3.53 mL, 3.53 mmol) at 25° C. was treated with a solution of 3-cyclopentyl-2-(3-methoxy-phenyl)-N-thiazol-2-yl-propionamide (prepared as in Example 110, 0.11 g, 0.35 mmol) in methylene chloride (3.5 mL). This solution was stirred at 25° C. for 1 h. At this time, the reaction was cooled to 0° C. and treated with a dilute aqueous ammonium hydroxide solution. This mixture was stirred at 0° C. for 15 min. At this time, the aqueous layer was separated from the organic layer. The aqueous layer was extracted with chloroform (3×50 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3-hydroxy-phenyl)-N-thiazol-2-yl-propionamide (50 mg, 44.7%) as a white solid: mp 177-179° C.; EI-HRMS m/e calcd for C17H20N2O2S (M+) −6.1245 found 316.1244.

Workup

  1. temperatureAt this time, the reaction was cooled to 0° C.
  2. stirringThis mixture was stirred at 0° C. for 15 min
  3. customAt this time, the aqueous layer was separated from the organic layer
  4. extractionThe aqueous layer was extracted with chloroform (3×50 mL)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd31a0813c6748ba9f9fc05ab9e6aae1
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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