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

HRID 445401ノート

反応式

HRID 445401 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fe401b0f21dc47f3a6cf69208aab73af
出典データセット
uspto-grants-2013_07
特許番号
US08476302B2

反応ノート

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