Borane → Methyl 3'-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylate

HRID 1069085노트

반응식

HRID 1069085 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>O1CCCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([O:27][CH3:28])=[O:26])[CH:20]=2)[CH:16]=[CH:17][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 6331BoraneHCID 54044428Methyl 3'-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1'-biphenyl]-3-carboxylate

생성물 1

HCID 21191174Methyl 3'-(2-(tert-butoxycarbonylamino)ethylamino)biphenyl-3-carboxylate수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To methyl 3′-[(2-[[(tert-butoxy)carbonyl]amino]acetylamino)]-[1,1′-biphenyl]-3-carboxylate (1.6 g) 0° C. was added a 1.0 M solution of borane in tetrahydrofuran (30 mL). The mixture was warmed to room temperature and stirred for 3 h. The mixture was quenched with saturated aqueous sodium bicarbonate and concentrated to leave a cloudy liquid that was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The separated organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography provided the title compound (740 mg). Electrospray MS (positive ion): M+Na 393.0

후처리

  1. customThe mixture was quenched with saturated aqueous sodium bicarbonate
  2. concentrationconcentrated
  3. customto leave a cloudy liquid that
  4. customwas partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  5. washThe separated organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-62cdd60502d8454b97074842ea184ee2
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06251925B1

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