左甲状腺素钠杂质 → 左旋沙丁胺醇

HRID 1455720

反应方程式

HRID 1455720 反应方程式
B.CSC.[CH3:5][C:6]([NH:9][CH2:10][CH:11]([C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18](OC)=[O:19])[OH:12])([CH3:8])[CH3:7].C1(C)C(C([C@@](C(O)=O)(O)[C@@](C(C2C(C)=CC=CC=2)=O)(O)C(O)=O)=O)=CC=CC=1.C1(C)C(C([C@](C(O)=O)(O)[C@](C(C2C(C)=CC=CC=2)=O)(O)C(O)=O)=O)=CC=CC=1>CO>[CH3:8][C:6]([NH:9][CH2:10][C@H:11]([OH:12])[C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH2:18][OH:19])[CH:22]=1)([CH3:5])[CH3:7]

参与物

6

反应物 4

HCID 11086725左甲状腺素钠杂质HCID 12423031(Dimethyl sulfide)trihydroboronHCID 129746773Ditoluoyl-l-tartaric acidHCID 129858806(+)-di-toluoyl-D-tartaric acid

产物 1

HCID 123600左旋沙丁胺醇

试剂、催化剂与溶剂 1

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂

实验过程

Several patents report synthetic routes using enantiomeric separation, however, the synthetic routes result in low yields of the enantiomerically pure product. Optically pure levalbuterol was synthesized by the borane-methylsulfide reduction of the enantiomerically pure precursor (Formula 2) as described in U.S. Pat. No. 5,399,765. The reaction dissolved a mixture of enantiomers of methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate and a chiral acid selected from (−)-di-toluoyl-L-tartaric acid and (+)-di-toluoyl-D-tartaric acid in methanol, upon cooling one stereoisomer crystallized, which was separated, and recrystallized as a diastereomer from methanol, the diastereomer was separated, treated with base, and upon reduction formed optically active levalbuterol.

后处理

  1. customseparation
  2. customhowever, the synthetic routes result
  3. customin low yields of the enantiomerically pure product
  4. dissolutionThe reaction dissolved
  5. temperatureupon cooling one stereoisomer crystallized, which
  6. customwas separated
  7. customrecrystallized as a diastereomer from methanol
  8. customthe diastereomer was separated
  9. additiontreated with base

来源与证据

ORD记录
ord-c07eb2839d6b4c14a590a0ea09564163
来源数据集
uspto-grants-2009_01
专利号
US07482489B2

关联笔记

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