(2S)-3-Phenylpropane-1,2-diamine → HCID 178428030、化合物

HRID 560914ノート

反応式

HRID 560914 の反応式
[C:1]1([CH2:7][C@H:8]([NH2:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Al](C)C.[F:16][C:17]1[CH:40]=[CH:39][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[S:31][C:30]([C:32](OCC)=O)=[C:29]([CH3:37])[CH:28]=3)[C:23]2=[O:38])=[CH:19][CH:18]=1>C1(C)C=CC=CC=1>[CH2:7]([CH:8]1[CH2:9][NH:10][C:32]([C:30]2[S:31][C:27]([N:24]3[CH2:25][CH2:26][N:22]([CH2:21][C:20]4[CH:39]=[CH:40][C:17]([F:16])=[CH:18][CH:19]=4)[C:23]3=[O:38])=[CH:28][C:29]=2[CH3:37])=[N:11]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 12699301(2S)-3-Phenylpropane-1,2-diamineHCID 16682925TrimethylaluminumHCID 58031706Ethyl 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate

生成物 1

HCID 178428030HCID 178428030、化合物収率 29%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a stirred solution of (S)-3-phenylpropane-1,2-diamine (0.37 g, 2.48 mmol) in toluene (20 mL) at 0° C. under nitrogen atmosphere was added dropwise trimethylaluminum (1.24 mL of 2.0 M solution in toluene, 2.48 mmol). When the fuming ceased, ethyl 5-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylate (0.60 g, 1.66 mmol) in toluene (5 mL) was added slowly. The resulting mixture was stirred at reflux for 18 h, cooled to ambient temperature and partitioned between ethyl acetate (75 mL) and water (50 mL). The aqueous layer was extracted with ethyl acetate (3×75 mL), and the combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with dichloromethane/methanol/triethyl amine (9/1/0.1) to afford the title compound as brown viscous oil in 29% yield (0.06 g): MS (ES+) m/z 449.2 (M+1).

後処理

  1. temperatureat reflux for 18 h
  2. custompartitioned between ethyl acetate (75 mL) and water (50 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×75 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography
  8. washeluted with dichloromethane/methanol/triethyl amine (9/1/0.1)

出典と根拠

ORDレコード
ord-3b2f6c1820a643cfa8e117e9cdbe91d6
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

反応ノート

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