Diisopropylethylamine → N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-phenyloctanamide

HRID 445401노트

반응식

HRID 445401 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:17][C:16]([CH2:18][NH2:19])=[N:15][N:14]=2)=[CH:9][CH:8]=1.[OH:23][CH:24]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:25](O)=[O:26].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C>CN(C)C=O.C([O-])(O)=O.[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:17][C:16]([CH2:18][NH:19][C:25](=[O:26])[CH:24]([OH:23])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)=[N:15][N:14]=2)=[CH:11][CH:12]=1

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 537335152-Hydroxy-8-phenyloctanoic acidHCID 66822259(5-(4-((3-Fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methanamine

생성물 1

HCID 66822711N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-phenyloctanamide

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A solution of (5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methanamine (0.85 mmol), 2-hydroxy-8-phenyloctanoic acid (0.85 mmol), 1-hydroxybenzotriazole hydrate (1.0 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.0 mmol), and DIPEA (3.4 mmol) in dimethylformamide (4 mL) was stirred at room temperature for 22 h. The resulting mixture was diluted with NaHCO3 (saturated) and extracted twice with ethyl acetate. The organic phases were combined, washed with brine, dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (MeOH—CH2Cl2) to yield N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-phenyloctanamide. A solution of N-((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)-2-hydroxy-8-phenyloctanamide (0.22 mmol) in CH2Cl2 (5 mL) was treated with the Dess-Martin periodinane (0.34 mmol) and stirred overnight. The resulting mixture was quenched with a solution of sodium thiosulfate dissolved in saturated aqueous NaHCO3, and the mixture was extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography (silica gel, heptane-ethyl acetate) to yield the title compound.

후처리

  1. extractionextracted twice with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (MeOH—CH2Cl2)

출처 및 근거

ORD 기록
ord-fe401b0f21dc47f3a6cf69208aab73af
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476302B2

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