Potassium Carbonate → Fmoc-Hyp(OEt)-OH

HRID 1482232ノート

反応式

HRID 1482232 の反応式
C([NH:3][C@@H:4]([CH2:8][C:9]1[CH:14]=CC=CC=1)[C:5]([OH:7])=[O:6])C.[C:15](=[O:18])([O-:17])[O-].[K+].[K+].C(=O)(ON1C(=O)CCC1=O)O[CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2.S(=O)(=O)(O)[O-].[K+].[O:52]1CCO[CH2:54][CH2:53]1>O>[CH:29]1[C:30]2[CH:35]([CH2:34][O:17][C:15]([N:3]3[CH2:14][C@H:9]([O:52][CH2:53][CH3:54])[CH2:8][C@H:4]3[C:5]([OH:7])=[O:6])=[O:18])[C:36]3[C:24](=[CH:23][CH:33]=[CH:32][CH:31]=3)[C:25]=2[CH:26]=[CH:27][CH:28]=1

参加物

7

反応物 5

HCID 11430Potassium CarbonateHCID 312751,4-Dioxane2 回HCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 516920Potassium bisulfateHCID 10566639(2S)-2-(ethylamino)-3-phenylpropanoic acid

生成物 1

HCID 89668655Fmoc-Hyp(OEt)-OH収率 37%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(S)-2-(Ethylamino)-3-phenylpropanoic acid (Compound SP442) (4.00 g, 20.7 mmol) was dissolved in a mixture of 1,4-dioxane (100 ml) and water (100 ml), potassium carbonate (8.69 g, 62.9 mmol) and (9H-fluoren-9-yl)methyl (2,5-dioxopyrrolidin-1-yl) carbonate (6.98 g, 20.7 mol) were added, and the mixture was stirred at room temperature for 8 hours. The aqueous layer was adjusted to pH 4 with a aqueous potassium bisulfate solution, and 1,4-dioxane was evaporated under reduced pressure. The resulting aqueous solution was extracted with ethyl acetate, and the resulting organic extract was washed with brine, dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by column chromatography (ethyl acetate:petroleum ether=1:1) to afford (2S,4R)-1-(((9H-fluoren-9-yl)methoxy)carbonyl)-4-ethoxypyrrolidine-2-carboxylic acid (Compound SP443) (3.2 g, 37%).

後処理

  1. additionwere added
  2. customwas evaporated under reduced pressure
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate
  4. extractionthe resulting organic extract
  5. washwas washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by column chromatography (ethyl acetate:petroleum ether=1:1)

出典と根拠

ORDレコード
ord-0ac5177e45b04cb3be332a56336c949c
出典データセット
uspto-grants-2016_08
特許番号
US09409952B2

反応ノート

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