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Dicyclohexylcarbodiimide → HCID 58542422, 화합물

HRID 1951910
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HRID 1951910 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 35890121-{[(Benzyloxy)carbonyl]amino}cyclopropane-1-carboxylic acidHCID 10535780(S)-methyl 2-(benzylamino)propanoate

생성물 1

HCID 58542422HCID 58542422, 화합물수율 71.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)]

출처 및 근거

ORD 기록
ord-a20576f1588845bb921f80a3459610b8
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08404691B2

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