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Dicyclohexylcarbodiimide → HCID 58542422、化合物

HRID 1951910
ノート
印刷プレビュー

反応式

HRID 1951910 の反応式
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([NH:23][C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:30]([O:37][C:38]([NH:40][C:41]1([C:44](O)=[O:45])[CH2:43][CH2:42]1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>ClCCl>[CH2:16]([N:23]([C:44]([C:41]1([NH:40][C:38]([O:37][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:39])[CH2:42][CH2:43]1)=[O:45])[C@H:24]([C:26]([O:28][CH3:29])=[O:27])[CH3:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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 10868DicyclohexylcarbodiimideHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 10535780(S)-methyl 2-(benzylamino)propanoate

生成物 1

HCID 58542422HCID 58542422、化合物収率 71.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

N,N′-dicyclohexylcarbodiimide (6.0 g, 29.0 mmol) was added to a dichloromethane (150 ml) solution of methyl N-benzyl-L-alaninate (5.20 g, 26.9 mmol) and 1-{[(benzyloxy)carbonyl]amino}cyclopropanecarboxylic acid (6.30 g, 26.7 mmol) under ice cooling and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure and then diluted with ethyl acetate, insoluble matter was removed by filtration and then the filtrate was washed with 1 N aqueous hydrochloric acid solution and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:3 (v/v)] to give the title compound (7.80 g, 71%) as a colorless oil.

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ethyl acetate, insoluble matter
  3. customwas removed by filtration
  4. washthe filtrate was washed with 1 N aqueous hydrochloric acid solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography [n-hexane:ethyl acetate=1:3 (v/v)]

出典と根拠

ORDレコード
ord-a20576f1588845bb921f80a3459610b8
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08404691B2

反応ノート

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