Methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoate → Levalbuterol

HRID 1455720

反応式

HRID 1455720 の反応式
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]

参加物

6

反応物 4

HCID 11086725Methyl 5-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-2-hydroxybenzoateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 129746773Ditoluoyl-l-tartaric acidHCID 129858806(+)-di-toluoyl-D-tartaric acid

生成物 1

HCID 123600Levalbuterol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c07eb2839d6b4c14a590a0ea09564163
出典データセット
uspto-grants-2009_01
特許番号
US07482489B2

関連ノート

読み込み中…