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

HRID 1455720

반응식

HRID 1455720 반응식
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]

참가 물질

6

반응물 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

생성물 1

HCID 123600Levalbuterol

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c07eb2839d6b4c14a590a0ea09564163
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482489B2

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