Chloroacetyl chloride → (5S)-1-(Chloroacetyl)-5-methyl-L-prolinamide

HRID 1293410Notes

Reaction equation

HRID 1293410 reaction equation
FC(F)(F)C(O)=O.[CH3:8][C@@H:9]1[NH:13][C@H:12]([C:14]([NH2:16])=[O:15])[CH2:11][CH2:10]1.C(N(CC)CC)C.[Cl:24][CH2:25][C:26](Cl)=[O:27].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:24][CH2:25][C:26]([N:13]1[C@@H:9]([CH3:8])[CH2:10][CH2:11][C@H:12]1[C:14]([NH2:16])=[O:15])=[O:27]

Participants

6

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 66757061HCID 66757061, compound

Product 1

HCID 45080982(5S)-1-(Chloroacetyl)-5-methyl-L-prolinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2S,5S)-5-Methyl-pyrrolidine-2-carboxylic acid amide trifluoroacetate (2.0 g, 8.2 mmol, Example 84D) and triethyl amine (1.9 mL, 24.6 mmol) were dissolved in CH2Cl2 (6 mL), and the mixture was cooled to 0° C. Chloroacetyl chloride (0.39 mL, 9.0 mmol) was added slowly via syringe. After 2 h, saturated NaHCO3 was added, and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried (Na2SO4), concentrated and purified by flash chromatography (10% MeOH/EtOAc) to give the title compound. MS (DCI) m/z 205 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-2dac35cd38be4379932498e2ec197752
Source dataset
uspto-grants-2007_07
Patent number
US07238724B2

Reaction notes

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