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4-Methylmorpholine → 2-[2-[2-Ethyl-4-(1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)piperazin-1-yl]-(4-chlorobenzyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 720189
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인쇄 미리보기

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HRID 720189 반응식
[ClH:1].[NH2:2][CH:3](CC1C=CC(Cl)=CC=1)[C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH:12]([CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[C:13]([NH:15][CH3:16])=[O:14])[CH2:8][CH:7]1[CH2:28][CH3:29])=[O:5].[C:38]([N:45]1[CH2:52][CH2:51][CH2:50][C@H:46]1[C:47]([OH:49])=O)([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39].[CH3:53]N(C)CCCN=C=NCC.ON1[C:69]2[CH:70]=[CH:71][CH:72]=[CH:73][C:68]=2N=N1.CN1CCOCC1>CN(C=O)C.O.CCOC(C)=O>[C:41]([O:40][C:38]([N:45]1[CH2:52][CH2:51][CH2:50][CH:46]1[C:47](=[O:49])[N:2]([CH2:53][C:68]1[CH:73]=[CH:72][C:71]([Cl:1])=[CH:70][CH:69]=1)[CH2:3][C:4]([N:6]1[CH2:11][CH2:10][N:9]([CH:12]([C:13](=[O:14])[NH:15][CH3:16])[CH2:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)[CH2:8][CH:7]1[CH2:28][CH3:29])=[O:5])=[O:39])([CH3:42])([CH3:43])[CH3:44]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 695874692-{4-[2-amino-3-(4-chlorophenyl)-propionyl]-3-ethyl-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propioamide HCl

생성물 1

HCID 69587921
2-[2-[2-Ethyl-4-(1-methylcarbamoyl-2-naphthalen-2-yl-ethyl)piperazin-1-yl]-(4-chlorobenzyl)-2-oxo-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

2-{4-[2-Amino-3-(4-chlorophenyl)-propionyl]-3-ethyl-piperazin-1-yl}-N-methyl-3-naphthalen-2-yl-propioamide HCl, 45, (0.5 g, 0.7 mmol) and Boc-L-proline (0.17 g, 0.78 mmol), 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide (0.19 g, 1.4 mmol) and 1-hydroxybenzotriazole (0.16 g, 0.86 mmol) are dissolved in anhydrous DMF (2.5 mL). The reaction mixture is cooled to 0° C., then N-methylmorpholine (0.6 mL, 5.3 mmol) is added. This reaction mixture is placed in a refrigerator overnight. EtOAc (25 mL) and water (75 mL) are added, and the organic layer is separated. The aqueous layer is extracted with EtOAc (3×30 mL). All organic layers are combined and washed with water (2×50 mL), and dried over Na2SO4. Solvent is removed in vacuo to afford 0.5 g of the desired product.

후처리

  1. customis placed in a refrigerator overnight
  2. customthe organic layer is separated
  3. extractionThe aqueous layer is extracted with EtOAc (3×30 mL)
  4. washwashed with water (2×50 mL)
  5. dry with materialdried over Na2SO4
  6. customSolvent is removed in vacuo

출처 및 근거

ORD 기록
ord-12140260d8bd4c5ca226870f112ac7bb
출처 데이터셋
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07132539B2

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