Dimethylamine → HCID 67428522, compound

HRID 490123Notes

Reaction equation

HRID 490123 reaction equation
Cl.[CH2:2]([N:4]=[C:5]=NCCCN(C)C)C.[C:13]([O:17][C:18]([N:20]1[CH2:27][C@@H:26]([F:28])[CH2:25][C@H:21]1[C:22](O)=[O:23])=[O:19])([CH3:16])([CH3:15])[CH3:14].O.ON1C2C=CC=CC=2N=N1.CNC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.CCCCCC.C(Cl)(Cl)Cl.O1CCCC1>[CH3:2][N:4]([CH3:5])[C:22]([C@@H:21]1[CH2:25][C@H:26]([F:28])[CH2:27][N:20]1[C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])=[O:23]

Participants

9

Reactant 5

HCID 674DimethylamineHCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756017(4S)-1-tert-Butoxycarbonyl-4-fluoro-L-prolineHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 67428522HCID 67428522, compoundYield 92.3%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

19.6 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added under ice cooling to a 200 mL tetrahydrofuran solution of 19.9 g of the compound obtained in step 2-2 and 17.3 g of 1-hydroxybenzotriazole monohydrate, and the reaction mixture was stirred for 30 minutes at the same temperature. After this, 9.24 g of a 50% dimethylamine aqueous solution was added to the reaction solution, and the reaction mixture was stirred for 1 hour while the temperature was raised to room temperature. 150 mL of solvent was distilled off under reduced pressure, and to the residue thus obtained was added 100 mL of chloroform and 100 mL of a 10% potassium carbonate aqueous solution. After liquid separation, the aqueous layer was extracted with chloroform, and the combined organic layer was washed with saturated brine and then dried with magnesium sulfate, after which the drying agent was filtered off and 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 20.5 g of the titled compound (colorless solid).

Workup

  1. stirringthe reaction mixture was stirred for 1 hour while the temperature
  2. distillation150 mL of solvent was distilled off under reduced pressure
  3. customto the residue thus obtained
  4. customAfter liquid separation
  5. extractionthe aqueous layer was extracted with chloroform
  6. washthe combined organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. filtrationafter which the drying agent was filtered off
  9. distillationthe solvent was distilled off under reduced pressure
  10. customThe residue thus obtained

Sources & evidence

ORD record
ord-a8d093fa87d34d5ba7a20fd124d90551
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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