Iodine → 1-(t-butoxycarbonyl)-4(N-acetyl-L-methionyl)piperazine

HRID 863657

反応式

HRID 863657 の反応式
[C:1]([NH:4][C@H:5]([C:10]([OH:12])=O)[CH2:6][CH2:7][S:8][CH3:9])(=[O:3])[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].II.C1C=C2C(C(O)(O)C(=O)C2=CC=1)=O>ClCl.ClCCl.C(O)(=O)C.O1CCCC1.C(#N)C>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([C:10](=[O:12])[C@H:5]([CH2:6][CH2:7][S:8][CH3:9])[NH:4][C:1](=[O:3])[CH3:2])[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

参加物

11

反応物 5

HCID 807IodineHCID 10236NinhydrinHCID 10868DicyclohexylcarbodiimideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 448580N-acetyl-L-methionine

生成物 1

HCID 544692851-(t-butoxycarbonyl)-4(N-acetyl-L-methionyl)piperazine収率 108.6%

試薬・触媒・溶媒 5

HCID 176Acetic Acid触媒HCID 6342Acetonitrile溶媒2 回HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒HCID 24526Chlorine溶媒

実験手順

A solution of 4.78 g (0.025 mol) of N-acetyl-L-methionine in CH2 Cl2 : acetonitrile (120 ml) was cooled to 0° C. To this solution was added 5.36 g (0.025 mol) of dicyclohexylcarbodiimide (DCC) followed by the rapid addition of 3.90 g (0.021 mol) of N-t-butoxycarbonylpiperazine in 6 ml of dichloromethane. The progress of the reaction was followed on silica gel TLC plates developed with 4:1 acetonitrile: tetrahydrofuran and visualized with either iodine or ninhydrin spray. The reaction was complete within 2 h. A few drops of glacial acetic acid were added to the reaction mixture and the solvent was removed on a rotary evaporator. The residue was taken up in ether and filtered. The clear filtrate was washed with dilute acid followed by dilute base. The organic layer was separated, dried over anhydrous sodium sulfate, filtered, and evaporated to give 8.2 g of 1-(t-butoxycarbonyl)-4-(N-acetyl-L-methionyl)piperazine, a colorless oil which required no further purification: IR (film) 3304, 3058, 2973, 2931, 2868, 1701, 1645, 1539, 1420, 1237, 1173 cm-1 ; NMR (CDCl3) δ 1.47 (s, 9 H), 1.80 (m, 2 H), 2.02 (s, 3 H), 2.10 (s, 3 H), 2.46 (m, 2 H), 3.53 (m, 8 H), 5.10 (M, 1 H), 6.35 (b, 0.5 H), 6.43 (b, 0.5 H).

後処理

  1. customthe solvent was removed on a rotary evaporator
  2. filtrationfiltered
  3. washThe clear filtrate was washed
  4. additionwith dilute acid
  5. additionby dilute base
  6. customThe organic layer was separated
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-328ba9ba46df41aebcb1abc9208b3ee4
出典データセット
uspto-grants-1998_02
特許番号
US05721365

関連ノート

読み込み中…