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 843733ノート

反応式

HRID 843733 の反応式
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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d7c9d268afa44dc3a8129143b0ad6cff
出典データセット
uspto-grants-2002_04
特許番号
US06380215B1

反応ノート

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