(2S)-3-Phenylpropane-1,2-diamine → HCID 178428030, 화합물

HRID 560914

반응식

HRID 560914 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 178428030HCID 178428030, 화합물수율 29%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3b2f6c1820a643cfa8e117e9cdbe91d6
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063084B2

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