Dimethylamine → HCID 25178383, compound

HRID 490127

Reaction equation

HRID 490127 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C:14]([F:17])([F:16])[CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:30]([N:32]=[C:33]=NCCCN(C)C)C.CNC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCC.C(Cl)(Cl)Cl.O1CCCC1>[CH3:30][N:32]([CH3:33])[C:10]([C@@H:9]1[CH2:13][C:14]([F:17])([F:16])[CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:11]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22977458(2S)-1-[(tert-butoxy)carbonyl]-4,4-difluoropyrrolidine-2-carboxylic acid

Product 1

HCID 25178383HCID 25178383, compoundYield 90.7%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A 40 mL tetrahydrofuran solution of 4.00 g of the compound obtained in step 3-3 and 3.23 g of 1-hydroxybenzotriazole monohydrate was stirred for 30 minutes under ice cooling. 3.66 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was then added, and the reaction mixture was stirred for 30 minutes at the same temperature. 2.15 g of a 50% dimethylamine aqueous solution was added to the reaction solution, after which the reaction mixture was stirred for 1 hour at room temperature. 60 mL of chloroform and 50 mL of a 5% potassium carbonate aqueous solution were added to the reaction solution, liquid separation was performed, the aqueous layer was extracted with chloroform (50 mL×2), the combined organic layer was washed with 30 mL of saturated brine and then dried with magnesium sulfate, and the drying agent was filtered off, after which the solvent was distilled off under reduced pressure. The residue thus obtained was subjected to column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=1/1 to 10/0; v/v) to obtain 4.02 g of the titled compound (colorless solid).

Workup

  1. stirringafter which the reaction mixture was stirred for 1 hour at room temperature
  2. extractionthe aqueous layer was extracted with chloroform (50 mL×2)
  3. washthe combined organic layer was washed with 30 mL of saturated brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationthe drying agent was filtered off
  6. distillationafter which the solvent was distilled off under reduced pressure
  7. customThe residue thus obtained

Sources & evidence

ORD record
ord-ac402e61351f4045b68b37ce04f0c827
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Linked notes

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