Acetic Acid → Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-hydroxyphenyl)-3-[(4-methoxybenzyl)thio]pentanoate

HRID 2101222

反応式

HRID 2101222 の反応式
C(O)(=O)C.[C:5]([O:9][C:10]([NH:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][CH:20]([CH:28]([S:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][Si](C(C)(C)C)(C)C)[CH:32]=2)[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:15][CH:14]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C([Si](OC1C=CC=C(I)C=1)(C)C)(C)(C)C.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[C:5]([O:9][C:10]([NH:12][C:13]1[N:18]=[CH:17][C:16]([CH2:19][CH:20]([CH:28]([S:45][CH2:46][C:47]2[CH:52]=[CH:51][C:50]([O:53][CH3:54])=[CH:49][CH:48]=2)[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)[C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:15][CH:14]=1)=[O:11])([CH3:6])([CH3:7])[CH3:8]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 27572803-(t-Butyldimethylsiloxy)iodobenzeneHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 69072378Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(4-methoxybenzyl)thio]pentanoate

生成物 1

HCID 69072041Tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-hydroxyphenyl)-3-[(4-methoxybenzyl)thio]pentanoate収率 98%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Glacial acetic acid (190 μL, 3.3 mmoL) was added to a solution of tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-3-[(4-methoxybenzyl)thio]pentanoate (800 mg, 0.89 mmol, synthesised according to the procedure for Example 1, starting from tert-butyl(3-iodophenoxy)dimethylsilane) in dry THF (10 mL). Tetrabutylammonium fluoride trihydrate (489 mg, 1.5 mmol) was added and the mixture was stirred for 12 h at room temperature. EtOAc (150 mL) was added and the solution was washed with saturated aqueous NaHCO3, water and brine, dried and concentrated. Flash chromatography (CH2Cl2/EtOAc, 10:1) gave tert-butyl 2-({6-[(tert-butoxycarbonyl)amino]pyridin-3-yl}methyl)-5-(3-hydroxyphenyl)-3-[(4-methoxybenzyl)thio]pentanoate (660 mg, 98%).

後処理

  1. customsynthesised
  2. washthe solution was washed with saturated aqueous NaHCO3, water and brine
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-c307d529028143bbbf89ae522e45c921
出典データセット
uspto-grants-2009_08
特許番号
US07572817B2

関連ノート

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