Piperidine → HCID 54258041、化合物

HRID 393475

反応式

HRID 393475 の反応式
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C([NH:39][C@@H:40]([C:48](O)=[O:49])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:48](=[O:49])[C@H:40]([NH2:39])[CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

参加物

8

反応物 5

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 978332(2R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-phenylpropanoic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 110118554-Amino-N-((1,1-dimethylethoxy)carbonyl)-L-phenylalanine methyl ester

生成物 1

HCID 54258041HCID 54258041、化合物収率 81.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

To the solution of 4-amino-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine methyl ester (5.09 g, 17 mmol) in DMF (60 mL) was added Fmoc-D-Phenylalanine (8.70 g, 22.5 mmol), DIPEA (12 mL, 69 mmol) and HBTU (8.50 g, 22.5 mmol). The mixture was then stirred at room temperature for 4 h. The reaction mixture was diluted with water (150 mL) and the light yellow solid which precipitated was collected by filtration. This solid was then redissolved in 60 mL of acetone and the solution was treated with 100 mL of water. The solid was collected by filtration and was washed with 1N HCl, H2O. After drying at 60° C. under vaccum overnight, a light yellow solid was obtained (13.2 g). A portion of this solid (2.51 g, 3.78 mmol) was dissolved in 15 mL of DMF and to the solution was added 1.5 mL of piperidine. The above solution was stirred at room temperature for 45 min. After removal of the solvent, the residue was recrystillized from ethyl acetate-hexane to give N-[(1,1-dimethylethoxy)carbonyl]-4-[[(2R)-2-amino-1-oxo-3-phenylpropyl]amino]-L-phenylalanine methyl ester (1.36 g, 3.0 mmol) in 81.5% yield. LR MS 442 (M+H).

後処理

  1. customthe light yellow solid which precipitated
  2. filtrationwas collected by filtration
  3. dissolutionThis solid was then redissolved in 60 mL of acetone
  4. additionthe solution was treated with 100 mL of water
  5. filtrationThe solid was collected by filtration
  6. washwas washed with 1N HCl, H2O
  7. customAfter drying at 60° C. under vaccum overnight
  8. customa light yellow solid was obtained (13.2 g)
  9. stirringThe above solution was stirred at room temperature for 45 min
  10. customAfter removal of the solvent

出典と根拠

ORDレコード
ord-cf1a60129f4c490ab85058eb4737f2bd
出典データセット
uspto-grants-2004_10
特許番号
US06806365B2

関連ノート

読み込み中…