Hydrochloric Acid → HCID 69884362、化合物

HRID 47793ノート

反応式

HRID 47793 の反応式
Cl.[CH3:2][O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](CCNCCCCCCC)[CH:8]=1.[F:27][C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=1[N:35]=[C:36]=[O:37].C([N:41]([CH2:45][CH3:46])[CH:42]([CH3:44])C)(C)C.Cl>C1(C)C=CC=CC=1>[CH3:2][O:3][C:4](=[O:26])[CH:5]([O:23][CH2:24][CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:46][CH2:45][N:41]([CH2:42][CH2:44][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[C:36]([NH:35][C:29]2[CH:30]=[CH:31][C:32]([F:34])=[CH:33][C:28]=2[F:27])=[O:37])=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 5932582,4-Difluorophenyl isocyanateHCID 698843992-ethoxy-3-[3-(2-heptylamino-ethyl)-phenyl]-propionic acid methyl ester HCl salt

生成物 1

HCID 69884362HCID 69884362、化合物収率 164.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 2-ethoxy-3-[3-(2-heptylamino-ethyl)-phenyl]-propionic acid methyl ester HCl salt (41 mg, 0.106 mmol), and 2,4-difluorophenylisocyanate (0.17 mmol, 0.0138 mL) in toluene (4.5 mL) was added N,N-diisopropylethylamine (0.32 mmol, 0.055 mL). The mixture was allowed to stir at room temperature for 18 hours, then was poured over 1M HCl (5 mL). The aqueous layer was isolated and extracted with diethyl ether (2×). The organic layers were combined, washed with 2M HCl (2×), brine (2×), dried over anhydrous sodium sulfate, and concentrated to give a clear oil. The crude solid was chromatographed on silica gel (Merck silica gel 60, art#9385-3) eluting with 20% ethyl acetate/hexanes to give 3-(4-{2-[3-(2,4-difluoro-phenyl)-1-heptyl-ureido]-ethyl}-phenyl)-2-ethoxy-propionic acid methyl ester as a clear oil (44 mg, 82%).

後処理

  1. customThe aqueous layer was isolated
  2. extractionextracted with diethyl ether (2×)
  3. washwashed with 2M HCl (2×), brine (2×)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give a clear oil
  7. customThe crude solid was chromatographed on silica gel (Merck silica gel 60, art#9385-3)
  8. washeluting with 20% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-ef472c2905ef43a5847a92465abb3c5a
出典データセット
uspto-grants-2004_03
特許番号
US06699904B2

反応ノート

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