Diisopropylcarbodiimide → N-alpha-Benzyloxycarbonyl-L-lysine

HRID 916522

반응식

HRID 916522 반응식
[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]

참가 물질

6

반응물 3

HCID 12734DiisopropylcarbodiimideHCID 24360CamptothecinHCID 18595285Dicarbobenzoxy-l-lysine

생성물 1

HCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b4763f1fae70488594e09ba58e389690
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07270808B2

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