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Dicyclohexylcarbodiimide → N-[(Phenylmethoxy)carbonyl]-D-histidyl-N-[2-(phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamide

HRID 1898979
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HRID 1898979 반응식
[C:1]([NH:11][C@@H:12]([C:19]([OH:21])=O)[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C1C=C2N=NN(O)C2=CC=1.O.C1CCC(N=C=NC2CCCCC2)CC1.[C:48]1([CH2:54][O:55][CH2:56][CH2:57][NH:58][C:59](=[O:77])[CH2:60][NH:61][CH2:62][C:63]2[CH:68]=[CH:67][C:66]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)=[CH:65][CH:64]=2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>CN(C=O)C>[C:5]1([CH2:4][O:3][C:1]([NH:11][C@@H:12]([C:19]([N:61]([CH2:62][C:63]2[CH:64]=[CH:65][C:66]([O:69][CH2:70][C:71]3[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=3)=[CH:67][CH:68]=2)[CH2:60][C:59]([NH:58][CH2:57][CH2:56][O:55][CH2:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:77])=[O:21])[CH2:13][C:14]2[N:18]=[CH:17][NH:16][CH:15]=2)=[O:2])[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70182186N-[2-(Phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamideHCID 178523878Z-D-His-OH

생성물 1

HCID 178521308N-[(Phenylmethoxy)carbonyl]-D-histidyl-N-[2-(phenylmethoxy)ethyl]-N2-[[4-(phenylmethoxy)phenyl]methyl]glycinamide수율 45%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

To a suspension of CBZ-D-histidine (0.093 g, 0.32 mmol) in DMF (2 mL) was added HOBT hydrate (0.059 g, 0.39 mmol) followed by DCC (0.080 g, 0.39 mmol). A solution of the compound from Step 3 above (0.13 g, 0.32 mmol) in DMF (2 mL) was added and the mixture was stirred overnight at room temperature. The mixture was filtered, and the filtrate was diluted with CHCl3, washed twice with saturated aqueous NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography (2-5% MeOH/CHCl3) gave 0.10 g (45%) of the title compound as a white powder; ES-MS 676 (m+1).

후처리

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with CHCl3
  3. washwashed twice with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a731391f76aa4670962998a005fc5a41
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05571792

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