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[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester → HCID 178454142, 화합물

HRID 227147
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HRID 227147 반응식
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:16](=O)[NH:17][C:18]1[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=1[NH2:25])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].C(OC(=O)N[C@H](C(=O)NC1C=C(I)C=CC=1N)CC1C=CC=CC=1)(C)(C)C>C(O)(=O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:16]1[NH:17][C:18]2[CH:23]=[CH:22][C:21]([I:24])=[CH:20][C:19]=2[N:25]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]
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4

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HCID 66815065[(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl esterHCID 66815291[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

생성물 1

HCID 178454142HCID 178454142, 화합물

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
65 °C

실험 절차

The mixture of regioisomers from step 2 {[(S)-1-(2-amino-4-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester and [(S)-1-(2-amino-5-iodo-phenylcarbamoyl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester} (1.0 g, 2.08 mmol) were dissolved in glacial acetic acid (30 mL) and heated to 65° C. for 1 hour. The reaction was cooled, concentrated in vacuo, basified with 10% w/v aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate (2×20 mL). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel eluted with 20% v/v ethyl acetate/hexanes to give [(S)-1-(5-iodo-1H-benzoimidazol-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester as a mixture of tautomers (950 mg, 99%).

후처리

  1. temperatureThe reaction was cooled
  2. concentrationconcentrated in vacuo
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography over silica gel
  9. washeluted with 20% v/v ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-4132ae36f9d74e539886968456c5848c
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07557221B2

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