2-Phenyl-3-isopropyl-5-[[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]methyl]oxazolidine → Betaxolol

HRID 845881

반응식

HRID 845881 반응식
C1(C2[N:11]([CH:12]([CH3:14])[CH3:13])[CH2:10][CH:9]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)=[CH:19][CH:18]=3)[O:8]2)C=CC=CC=1>C(O)(C)C.Cl>[CH3:14][CH:12]([NH:11][CH2:10][CH:9]([OH:8])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][CH:27]2[CH2:29][CH2:28]2)=[CH:19][CH:18]=1)[CH3:13]

참가 물질

4

반응물 1

HCID 141218512-Phenyl-3-isopropyl-5-[[4-[2-(cyclopropylmethoxy)ethyl]phenoxy]methyl]oxazolidine

생성물 1

HCID 2369Betaxolol

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 3776Isopropanol용매

실험 절차

2.25 g of 2-Phenyl-3-isopropyl-5-[[4-[2-(cyclopropyl methoxy)ethyl]phenoxy]methyl]oxazolidine from Example 4 was dissolved in a mixture of 10 mLs isopropanol, 10 mLs 5% aqueous hydrochloric acid. It was stirred at room temperature for 16 hrs. The isopropanol was removed under reduced pressure and 30 mLs 1% hydrochloric acid was added. The aqueous phase was washed with 15 mLs of toluene then basified and extracted twice with 10 mL portions of toluene. After removal of the solvent under reduced pressure 1.3 g of white solid was obtained (74% crude yield of betaxolol base). Betaxolol base was converted into its hydrochloride salt by dissolution in toluene and treatment with 1 equivalent of hydrochloric acid in isopropanol. Upon removal of isopropanol under reduced pressure and cooling of the toluene solution the hydrochloride salt of betaxolol was obtained. This solid is recrystallized twice from acetone, 4 mL/g, the second time with charcoal treatment to give a white crystalline solid with a melting point of 111.5°-112.5° C.

후처리

  1. customThe isopropanol was removed under reduced pressure and 30 mLs 1% hydrochloric acid
  2. additionwas added
  3. washThe aqueous phase was washed with 15 mLs of toluene
  4. extractionextracted twice with 10 mL portions of toluene
  5. customAfter removal of the solvent under reduced pressure 1.3 g of white solid

출처 및 근거

ORD 기록
ord-abac4399f6194e2388098376917edde2
출처 데이터셋
uspto-grants-1988_07
특허 번호
US04760182

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