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

HRID 1069085ノート

反応式

HRID 1069085 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-62cdd60502d8454b97074842ea184ee2
出典データセット
uspto-grants-2001_06
特許番号
US06251925B1

反応ノート

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