Hydrochloric Acid → Topotecan Hydrochloride

HRID 1012045

반응식

HRID 1012045 반응식
[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[C:16]([CH:17]=[C:18]([OH:26])[CH:19]=[CH:20]2)=[CH:15][C:14]=1[CH2:13]3)=[O:11].[Cl:28]CCl.Cl>C(O)(C)C.C(N(CC)CC)C>[CH3:1][CH2:2][C@@:3]1([OH:27])[C:8](=[O:9])[O:7][CH2:6][C:5]2[C:10]([N:12]3[C:24](=[CH:25][C:4]1=2)[C:23]1[N:22]=[C:21]2[CH:20]=[CH:19][C:18]([OH:26])=[C:17]([CH2:10][N:12]([CH3:24])[CH3:13])[C:16]2=[CH:15][C:14]=1[CH2:13]3)=[O:11].[ClH:28]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 97226Hydroxycamptothecin

생성물 1

HCID 60699Topotecan Hydrochloride수율 238.7%

시약·촉매·용매 2

HCID 3776Isopropanol용매2회HCID 8471Triethylamine용매

반응 조건

온도
27.5 °C

실험 절차

10-hydroxy-camptothecin (1.0 kg), dichloromethane (about 13 kg) and isopropanol (about 8 kg) were charged into a suitable reactor. N,N-dimethylmethyleneiminium chloride (0.3-0.5 kg) was added into the reactor. Triethylamine (0.04-0.2 kg) was then added into the resulting mixture at 20-35° C. and stirred at 20-35° C. for at least 12 hours. When the reaction was complete, a mixture of hydrochloric acid (32%, 0.06-0.3 kg) and isopropanol (about 5 kg) was added into the resulting mixture. After the addition was completed, the resulting mixture was stirred, filtered, and then washed with dichloromethane (about 3 kg). The wet solids were dried to give about 1.5 kg of crude topotecan HCl.

후처리

  1. additionwas added into the resulting mixture
  2. additionAfter the addition
  3. stirringthe resulting mixture was stirred
  4. filtrationfiltered
  5. washwashed with dichloromethane (about 3 kg)
  6. customThe wet solids were dried

출처 및 근거

ORD 기록
ord-a990f31caf2b42d798fbefd3670a4b58
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977483B2

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