Salbutamol → [(1,1-Dimethylethyl)(phenylmethyl)-amino]acetyl-2-hydroxybenzoate

HRID 1710226

反応式

HRID 1710226 の反応式
CC(NCC(O)C1C=CC(O)=C(CO)C=1)(C)C.C(C1C=CC=CC=1)(=O)C.Br[CH2:28][C:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[OH:39])=[O:30].[CH3:41][C:42]([NH:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([CH3:44])[CH3:43]>>[CH3:44][C:42]([N:45]([CH2:28][C:29]([O:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[OH:39])=[O:30])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)([CH3:41])[CH3:43]

参加物

5

反応物 4

HCID 2083SalbutamolHCID 7410AcetophenoneHCID 76908N-(1,1-Dimethylethyl)benzenemethanamineHCID 21684415Bromoacetyl-2-hydroxybenzoate

生成物 1

HCID 86744191[(1,1-Dimethylethyl)(phenylmethyl)-amino]acetyl-2-hydroxybenzoate

実験手順

Albuterol has been prepared, see Irish Patent Specification No. 31391, Aug. 9, 1972, starting from the appropriate acetophenone derivative methyl-5-(bromoacetyl-2-hydroxybenzoate, by condensation with N-(1,1-dimethylethyl)benzenemethanamine in the presence of base to form the ketonic ester, methyl-5[[(1,1-dimethylethyl)(phenylmethyl)-amino]acetyl-2-hydroxybenzoate. The ketonic ester is reduced with lithium aluminum hydride in tetrahydrofuran under nitrogen to yield α1-[[(1,1-dimethylethyl)-(phenylmethyl)amino]methyl]-4-hydroxy-1,3-benzenedimethanol which is subsequently debenzylated with hydrogen in the presence of palladium on carbon catalyst to produce albuterol.

出典と根拠

ORDレコード
ord-a7ee21119a7b4553868bb6ad80262184
出典データセット
uspto-grants-1990_08
特許番号
US04952729

関連ノート

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