1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-beta-alanine ethyl ester

HRID 843733노트

반응식

HRID 843733 반응식
Cl.NC[CH:4](C#C)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][C:27]([N:29]2[CH2:34][CH2:33][CH2:32][C@@H:31](C(O)=O)[CH2:30]2)=[O:28])[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[OH:38]N1C2C=CC=CC=2N=N1.C(N=C=N[CH2:53][CH2:54][CH2:55][N:56]([CH3:58])C)C>CN(C)C=O.O>[CH2:8]([O:7][C:5](=[O:6])[CH2:4][CH:55]([C:54]#[CH:53])[NH:56][C:58]([C@@H:31]1[CH2:32][CH2:33][CH2:34][N:29]([C:27](=[O:28])[CH2:26][CH2:25][CH:22]2[CH2:21][CH2:20][N:19]([C:17]([O:16][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:18])[CH2:24][CH2:23]2)[CH2:30]1)=[O:38])[CH3:9]

참가 물질

7

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 22611856Ethyl 3-amino-2-ethynylpropionate hydrochlorideHCID 54408184(R)-1-(3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl]-3-piperidinecarboxylic acid

생성물 1

HCID 86584068N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-beta-alanine ethyl ester

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a mixture of ethyl 3-amino-2-ethynylpropionate hydrochloride (0.5 g), (R)-1-[3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl]-3-piperidinecarboxylic acid (1.04 g) and 1-hydroxybenztriazole (0.38 g) in N,N-dimethylformamide (5 ml) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (0.51 ml) under stirring at 0° C. After stirring at ambient temperature overnight, the mixture was poured into water and extracted with ethyl acetate. The extract was washed with water, brine and dried over MgSO4, and evaporated in vacuo. The residue was purified by chromatography on silica gel eluting with CHCl3:MeOH=(100:1) to give N-[(R)-1-{3-(1-tert-butoxycarbonyl-4-piperidyl)propionyl}-3-piperidylcarbonyl]-3-ethynyl-β-alanine ethyl ester as an oil (1.38 g).

후처리

  1. stirringAfter stirring at ambient temperature overnight
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography on silica gel eluting with CHCl3

출처 및 근거

ORD 기록
ord-d7c9d268afa44dc3a8129143b0ad6cff
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380215B1

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