Hydrochloric Acid → Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoate

HRID 2422317

反応式

HRID 2422317 の反応式
[CH:1]([C:4]1[N:5]=[C:6]([NH:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:3])[CH3:2].[H-].[Na+].Cl[CH2:18][C:19]1[CH:38]=[CH:37][C:22]([CH2:23][O:24][C:25]2[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=2)=[CH:21][CH:20]=1.Cl>O.CN(C)C=O>[CH:1]([C:4]1[N:5]=[C:6]([N:9]([CH2:18][C:19]2[CH:38]=[CH:37][C:22]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][C:33]([O:35][CH3:36])=[O:34])=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[S:7][CH:8]=1)([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 23082857Methyl 3-(4-([4-(chloromethyl)benzyl]oxy)phenyl)propanoateHCID 230830994-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine

生成物 1

HCID 57541858Methyl 3-{4-[(4-{[(4-isopropyl-1,3-thiazol-2-yl)(3-methylbutyl)amino]methyl}benzyl)oxy]phenyl}propanoate収率 30.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-isopropyl-N-(3-methylbutyl)-1,3-thiazol-2-amine (313 mg), sodium hydride (60% oil, 50 mg) and N,N-dimethylformamide (5 mL) was stirred at room temperature for 1 hr. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (318 mg) was added to the reaction mixture, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water, acidified with 1N aqueous hydrochloric acid solution, and extracted with ethyl acetate. The ethyl acetate layer was dried using Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.), and concentrated. The residue was purified by preparative HPLC (gradient cycle A) to give the title compound (150 mg, yield 28%) as a yellow oil.

後処理

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe ethyl acetate layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (gradient cycle A)

出典と根拠

ORDレコード
ord-8f63154f9215437d896ab3bd116e09bb
出典データセット
uspto-grants-2011_06
特許番号
US07960369B2

関連ノート

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