Ethylene Oxide → 1-(2-Hydroxy-ethyl)-4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-propyl-tetrahydro-pyran-2-yl)-propyl]-amide

HRID 1269025

반응식

HRID 1269025 반응식
[CH2:1]1[O:3][CH2:2]1.[CH3:4][CH:5]([CH3:32])[CH:6]([NH:19][C:20]([CH:22]1[CH2:26][CH:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][NH:23]1)=[O:21])[CH:7]1[CH:12]([OH:13])[CH:11]([OH:14])[CH:10]([OH:15])[CH:9]([CH2:16][CH2:17][CH3:18])[O:8]1>CO.CCOCC>[CH3:32][CH:5]([CH3:4])[CH:6]([NH:19][C:20]([CH:22]1[CH2:26][CH:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][N:23]1[CH2:1][CH2:2][OH:3])=[O:21])[CH:7]1[CH:12]([OH:13])[CH:11]([OH:14])[CH:10]([OH:15])[CH:9]([CH2:16][CH2:17][CH3:18])[O:8]1

참가 물질

5

반응물 2

HCID 6354Ethylene Oxide2회HCID 112237364-Pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-propyl-tetrahydro-pyran-2-yl)-propyl]-amide

생성물 1

HCID 113170811-(2-Hydroxy-ethyl)-4-pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-propyl-tetrahydro-pyran-2-yl)-propyl]-amide수율 34%

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

The title compound was prepared according to the process illustrated in Scheme 19. Ethylene oxide was used as the alkylating agent. To a stirred solution of 4-Pentyl-pyrrolidine-2-carboxylic acid [2-methyl-1-(3,4,5-trihydroxy-6-propyl-tetrahydro-pyran-2-yl)-propyl]-amide (example 103) (12.0 mg 0.029 mmol, 1 equiv) and TEA (100 μL) in MeOH (2 mL) at 0° C. was added condensed ethylene oxide (200 μL) was added and the reaction mixture stirred 48 h. The reaction mixture evaporated to dryness, and the resulting residue was purified by column chromatography on silica 20% 0.25M NH3 in MeOH/DCM to give the crude N alkylated product. The crude product was taken up in Et2O, filtered and the filtrate treated with 2M HCl in Et2O, the precipetated HCl salt was collected washed with Et2O and lyophylized to give the title compound as a colorless powder (4.4 mg 34%).

후처리

  1. customThe title compound was prepared
  2. additionwas added
  3. customThe reaction mixture evaporated to dryness
  4. customthe resulting residue was purified by column chromatography on silica 20% 0.25M NH3 in MeOH/DCM
  5. customto give the crude N
  6. filtrationfiltered
  7. additionthe filtrate treated with 2M HCl in Et2O
  8. customthe precipetated HCl salt was collected
  9. washwashed with Et2O

출처 및 근거

ORD 기록
ord-c0c28630e8124bca83713109fa33e00d
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199106B2

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