p-Toluenesulfonic acid → 2-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

HRID 1779822ノート

反応式

HRID 1779822 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N[C:17](=[O:52])[C@H:18]([CH3:51])[CH2:19][C@H:20]([OH:50])[C@@H:21]([NH:42][C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:22][C@@H:23]([CH:39]([CH3:41])[CH3:40])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)CCC>C(Cl)(Cl)Cl>[C:46]([O:45][C:43]([NH:42][C@H:21]([CH:20]1[CH2:19][C@@H:18]([CH3:51])[C:17](=[O:52])[O:50]1)[CH2:22][C@@H:23]([CH:39]([CH3:40])[CH3:41])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH2:34][CH2:35][CH2:36][O:37][CH3:38])[CH:26]=1)=[O:44])([CH3:49])([CH3:48])[CH3:47]

参加物

4

反応物 2

HCID 6101p-Toluenesulfonic acidHCID 236251841,1-Dimethylethyl N-((1S,2S,4R)-5-(butylamino)-2-hydroxy-1-((2S)-2-((4-methoxy-3-(3-methoxypropoxy)phenyl)methyl)-3-methylbutyl)-4-methyl-5-oxopentyl)carbamate

生成物 1

HCID 228657322-{1 (S)-tert-butoxycarbonylamino-3(S)-isopropyl-4-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-butyl}-4(R)-methyl-tetrahydrofuran-5-one

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

2.02 g of p-toluenesulfonic acid (monohydrate) are added to 5.6 g of 5(S)-tert-butoxycarbonylamino-4(S)-hydroxy-7(S)-isopropyl-2(R)-methyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid (N-butyl)-amide (Example 32) in 240 ml of chloroform at room temperature and the mixture is stirred at room temperature for a further 18 hours. The reaction mixture is concentrated by evaporation and the residue is partitioned between diethyl ether and 0.1N hydrochloric acid. The organic phases are concentrated by evaporation and the title compound is obtained from the residue after FC (160 g of silica gel, eluant: ethyl acetate/hexane 1:1): Rf (ethyl acetate/hexane=2:1)=0.47; m.p. 86°-87° C.

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. customthe residue is partitioned between diethyl ether and 0.1N hydrochloric acid
  3. concentrationThe organic phases are concentrated by evaporation

出典と根拠

ORDレコード
ord-aa01b9c15dd44b868209370325ed2ac2
出典データセット
uspto-grants-1997_05
特許番号
US05627182

反応ノート

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