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Phenyl isocyanate → Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

HRID 557273
ノート
印刷プレビュー

反応式

HRID 557273 の反応式
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:24]([CH2:27][CH2:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:31][CH:30]=1)([O-])=[O:25].C(N(CC)CC)C.C1(N=C=O)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:25][N:24]=[C:27]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:41][CH:42]=3)[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridineHCID 59841574tert-butyl N-[(tert-butoxy)carbonyl]-N-(3-ethynylpyridin-2-yl)carbamate

生成物 1

HCID 25114167Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Under stirring at 50° C, to a solution of di-tert-butyl(3-ethinyl pyridin-2-yl)imidodicarbonate described in Preparation Example 3-1-1 (2.0 g), 2-(4-(2-nitro-ethyl)-benzyloxy) pyridine described in Preparation Example 1-3-4 (2.44 g), triethylamine (0.086 uL) and tetrahydrofuran (20 mL) was added phenyl isocyanate (2.8 mL) divided into four portions over 5.5 hours. After the additions were finished, stirring was carried out at 50° C for another two hours. NH-silica gel was added to the reaction solution, and the solvent was concentrated under a reduced pressure. The resulting residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=3:1). The resulting solution was concentrated under a reduced pressure and purified by silica gel chromatography (heptane:ethyl acetate=3:1 then 2:1) to obtain the title compound (2.2 g).

後処理

  1. waitwas carried out at 50° C for another two hours
  2. additionNH-silica gel was added to the reaction solution
  3. concentrationthe solvent was concentrated under a reduced pressure
  4. customThe resulting residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=3:1)
  5. concentrationThe resulting solution was concentrated under a reduced pressure
  6. custompurified by silica gel chromatography (heptane

出典と根拠

ORDレコード
ord-0ef0cdc571634133949460000f5162bc
出典データセット
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08058444B2

反応ノート

読み込み中…

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