Dimethylamine → HCID 25178383, 화합물

HRID 490127

반응식

HRID 490127 반응식
[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]

참가 물질

9

반응물 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

생성물 1

HCID 25178383HCID 25178383, 화합물수율 90.7%

시약·촉매·용매 3

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ac402e61351f4045b68b37ce04f0c827
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528124B2

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