Triethylamine → HCID 57986839、化合物

HRID 871915ノート

反応式

HRID 871915 の反応式
[CH2:1]([O:8][CH2:9][C:10]([OH:12])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.C(OC(Cl)=O)C(C)C.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41](=[NH:44])[NH:42]O)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][CH:38]([C:41]2[N:44]=[C:10]([CH2:9][O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[O:12][N:42]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 290301(Benzyloxy)acetic acidHCID 178451986HCID 178451986、化合物

生成物 1

HCID 57986839HCID 57986839、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of benzyloxy-acetic acid (5 g, 30 mmol), NEt3 (3.6 g, 36 mmol) in toluene (150 mL) was added isobutylchloroformate (4.1 g, 30 mmol) at 0° C. The mixture was stirred at room temperature for 1.5 hours. 4-(N-hydroxycarbamimidoyl)-piperidine-1-carboxylic acid tert-butyl ester (7.3 g, 30 mmol) was added to the mixture. The mixture was heated under reflux overnight, cooled and the mixture was washed successively with H2O and brine. After drying (Na2SO4), the solvent was removed. The residue was purified by flash chromatography on silica gel to afford the desired product. 1H NMR (CDCl3): δ 7.4˜7.3 (5H, m), 4.7 (2H, s), 4.69 (2H, s), 4.2˜4.04 (2H, m), 3.02˜2.84 (3H, m), 2.04˜1.94 (2H, m), 1.84˜1.7 (2H, m), 1.46 (9H, s).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux overnight
  3. temperaturecooled
  4. washthe mixture was washed successively with H2O and brine
  5. dry with materialAfter drying (Na2SO4)
  6. customthe solvent was removed
  7. customThe residue was purified by flash chromatography on silica gel

出典と根拠

ORDレコード
ord-4f40c99446004891b0cb320e2b75c321
出典データセット
uspto-grants-2015_03
特許番号
US08975258B2

反応ノート

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