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Phenylalanine anilide → HCID 90045798、化合物

HRID 1189918
ノート
印刷プレビュー

反応式

HRID 1189918 の反応式
CCN=C=NCCCN(C)C.Cl.[NH:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:14]([C:17]([OH:19])=O)([CH3:16])[CH3:15].[NH2:27][C@H:28]([C:36]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1>[NH:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:14]([C:17]([NH:27][C@H:28]([C:36]([NH:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:19])([CH3:15])[CH3:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 151952Phenylalanine anilideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

生成物 1

HCID 90045798HCID 90045798、化合物収率 92.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4.04 g (22.1 mmol) of EDCl was added to 60 ml of THF solution of 2.99 g (14.7 mmol) of Boc-Aib-OH (manufactured by Sigma-Aldrich Corporation), and 3.53 g (14.7 mmol) of H-Phe-NHPh obtained in Synthesis Example 6-2, followed by stirring for 6 hours at room temperature. After a reaction mixture was concentrated under reduced pressure, the concentrate was extracted by adding water and ethyl acetate. After an organic layer was washed sequentially with a diluted hydrochloric acid, an aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure, thereby obtaining crude amide. The obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio)), thereby obtaining 5.79 g of the product with a yield of 92.6%.

後処理

  1. customobtained in Synthesis Example 6-2
  2. concentrationAfter a reaction mixture was concentrated under reduced pressure
  3. extractionthe concentrate was extracted
  4. additionby adding water and ethyl acetate
  5. washAfter an organic layer was washed sequentially with a diluted hydrochloric acid
  6. concentrationan aqueous solution of sodium hydrogen carbonate and water (one time for each), it was concentrated under reduced pressure
  7. customobtaining crude amide
  8. customThe obtained amide compound was purified by a silica gel column chromatography (hexane/ethyl acetate=5/1 to 1/1 (volume ratio))

出典と根拠

ORDレコード
ord-c332a340758f40d2a2435756734a280d
出典データセット
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08674144B2

反応ノート

読み込み中…

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