Dimethylformamide → 4-(Cbz-amino)benzaldehyde

HRID 1179484노트

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HRID 1179484 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:27]=[O:28])C>C1COCC1>[CH:27]([C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1)=[O:28]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 561232Benzyl 4-bromophenylcarbamateHCID 178418339Butyllithium

생성물 1

HCID 125537634-(Cbz-amino)benzaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Benzyl 4-bromophenylcarbamate (20 g, 65.3 mmol) was taken in anhydrous THF (440 mL) and cooled to −78° C. To this solution, n-BuLi (55 mL, 137.2 mmol) was added dropwise and stirred for 0.5 h at −78° C. To this mixture, DMF (7.6 mL) was added dropwise and the reaction was allowed to warm to room temperature over a period of 5 h. The reaction mixture was quenched with 1 N HCl and then concentrated to remove THF, followed by addition of water. The mixture was extracted with three portions of ethyl acetate. The combined organic phases were washed with H2O, brine, and dried (MgSO4) filtered and concentrated. Trituration with hexanes and then with 20% ethyl acetate in hexanes afforded the title compound as a yellow solid.

후처리

  1. temperatureto warm to room temperature over a period of 5 h
  2. customThe reaction mixture was quenched with 1 N HCl
  3. concentrationconcentrated
  4. customto remove THF
  5. additionfollowed by addition of water
  6. extractionThe mixture was extracted with three portions of ethyl acetate
  7. washThe combined organic phases were washed with H2O, brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-95b06fa033a346b28d1ab4212403a9f4
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279494B2

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