Hydrochloric Acid → Topotecan Hydrochloride

HRID 1012045

反応式

HRID 1012045 の反応式
[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]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 97226Hydroxycamptothecin

生成物 1

HCID 60699Topotecan Hydrochloride収率 238.7%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒2 回HCID 8471Triethylamine溶媒

反応条件

温度
27.5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a990f31caf2b42d798fbefd3670a4b58
出典データセット
uspto-grants-2011_07
特許番号
US07977483B2

関連ノート

読み込み中…