Diisopropylcarbodiimide → N-alpha-Benzyloxycarbonyl-L-lysine

HRID 916522

反応式

HRID 916522 の反応式
[C:1]([N:11](C(OCC1C=CC=CC=1)=O)[C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(C)N=C=NC(C)C.CC[C@@]1(O)C(=O)OCC2C(N3C(=CC1=2)C1N=C2C(C=CC=C2)=CC=1C3)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[NH:11]([C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17]

参加物

6

反応物 3

HCID 12734DiisopropylcarbodiimideHCID 24360CamptothecinHCID 18595285Dicarbobenzoxy-l-lysine

生成物 1

HCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

N,N-Bis CBZ-Lysine (311 mg, 0.75 mmol) was dissolved in 56 mL of anhydrous methylene chloride at room temperature. To this solution were added DIPC (0.12 mL, 0.75 mmol), DMAP (0.61 mg, 0.5 mmol) and camptothecin (0.087 g, 0.25 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and left for 16 h. The solution was washed with 0.1 N HCl, dried and evaporated under reduced pressure to yield a light yellow solid, which was recrystallized from methanol to give camptothecin-20-ester of N,N-Bis CBZ-Lys 13. Purification of 13 was satisfactory based on TLC and HPLC analysis.

後処理

  1. washThe solution was washed with 0.1 N HCl
  2. customdried
  3. customevaporated under reduced pressure
  4. customto yield a light yellow solid, which
  5. customwas recrystallized from methanol

出典と根拠

ORDレコード
ord-b4763f1fae70488594e09ba58e389690
出典データセット
uspto-grants-2007_09
特許番号
US07270808B2

関連ノート

読み込み中…