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Triethylamine → 1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]-amide

HRID 1295671
ノート
印刷プレビュー

反応式

HRID 1295671 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]2)[C:5]([Cl:15])=[CH:4][N:3]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[CH:37]1[CH:42]=[C:41]([Cl:43])[CH:40]=[C:39]([C@H:44]([NH2:47])[CH2:45][OH:46])[CH:38]=1.C(N(CC)CC)C>CN(C=O)C.C(OCC)(=O)C>[Cl:43][C:41]1[CH:40]=[C:39]([CH:44]([NH:47][C:12]([CH:10]2[CH2:9][N:8]([C:6]3[C:5]([Cl:15])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH2:11]2)=[O:14])[CH2:45][OH:46])[CH:38]=[CH:37][CH:42]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 59694427(S)-2-amino-2-(3-chlorophenyl)ethanolHCID 878230181-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid

生成物 1

HCID 90894357
1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid [1-(3-chlorophenyl)-2-hydroxyethyl]-amide
収率 41%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1-(2,5-Dichloropyrimidin-4-yl)-azetidine-3-carboxylic acid (66 mg, 0.27 mmol, 1 equivalent) was dissolved in DMF (1 mL) together with EDCI (103 mg, 0.53 mmol, 2 equivalents), HOBt (18 mg, 0.13 mmol, 0.5 equivalent) and (S)-(+)-3-chlorophenylglycinol (67.4 mg, 0.32 mmol, 1.2 equivalents). Triethylamine (121 mg, 0.32 mmol, 1.2 equivalents) was then added and the resulting mixture was stirred at room temperature for 1 hour then warmed to 90° C. for 10 minutes. The crude reaction mixture was diluted with ethyl acetate, washed with water, and the organic fraction dried over sodium sulfate. The resulting crude oil was purified by HPLC Gilson (acetonitrile/water/0.1% TFA), yielding the title compound as a white solid (44 mg, 41%). HPLC Rt=5.528 minutes.

後処理

  1. temperaturethen warmed to 90° C. for 10 minutes
  2. customThe crude reaction mixture
  3. washwashed with water
  4. dry with materialthe organic fraction dried over sodium sulfate
  5. customThe resulting crude oil was purified by HPLC Gilson (acetonitrile/water/0.1% TFA)

出典と根拠

ORDレコード
ord-32d67224295841c69a7cb4105f0101f4
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07244735B2

反応ノート

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