Benzylamine → Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine benzylamide

HRID 64644ノート

反応式

HRID 64644 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:23][CH:24]([CH3:26])[CH3:25])[C@@H:10]([OH:22])[CH2:11][CH2:12][NH:13][C@H:14]([C:19]([OH:21])=O)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C([O-])(O)=O.[Na+].[N-]=[N+]=[N-].[Na+].C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1>CN(C=O)C>[CH2:27]([NH:34][C:19](=[O:21])[C@H:14]([CH2:15][CH:16]([CH3:17])[CH3:18])[NH:13][CH2:12][CH2:11][C@H:10]([OH:22])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:23][CH:24]([CH3:26])[CH3:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 5

HCID 7504BenzylamineHCID 33557Sodium AzideHCID 199401P,P-Diphenylphosphinic azideHCID 516892Sodium BicarbonateHCID 13672673Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine

生成物 1

HCID 18604257Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine benzylamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-30 °C

実験手順

3 (540 mg) was suspended in DMF (23 ml) and treated with benzylamine (0.374 ml), TEA (0.401 ml), NaHCO3 (solid) (924 mg) and sodium azide (117 mg). The suspension was cooled to -30° C., treated with DPPA (0.934 ml), and stirred at 0° C. for 72 hours. After removal of the DMF in vacuo, the residue was treated with 10% citric acid and extracted with EtOAc (3x). The combined extracts were washed with 10% citric acid (1x), H2O (1x), 10% NaHCO3 (aqueous) (1x), and brine (1x), dried over MgSO4, filtered and evaporated to dryness in vacuo to give a crude colorless oil (1.5 g). Flash chromatography on silica gel (90/10/1/1 of CH2Cl2 /MeOH/H2O/HOAc) gave 7 as a sticky foam (440 mg).

後処理

  1. customAfter removal of the DMF in vacuo
  2. additionthe residue was treated with 10% citric acid
  3. extractionextracted with EtOAc (3x)
  4. washThe combined extracts were washed with 10% citric acid (1x), H2O (1x), 10% NaHCO3 (aqueous) (1x), and brine (1x)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customto give a crude colorless oil (1.5 g)

出典と根拠

ORDレコード
ord-b657b476726f4db8943f449aeab25c95
出典データセット
uspto-grants-1986_09
特許番号
US04609641

反応ノート

読み込み中…