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Sodium Hydroxide → Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate

HRID 219983
ノート
印刷プレビュー

反応式

HRID 219983 の反応式
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=3)[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29].Br[CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[OH-].[Na+]>C1(C)C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[O:14][N:13]=[C:12]([C:15]3[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=3)[CH2:21][O:22][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[N:11]=2)[CH:7]=[CH:6][C:5]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH3:29]
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 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 59495704(3-{5-[2-(Methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol

生成物 1

HCID 86645659Tert-butyl [(3-{5-[2-(methoxymethyl)-2'-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzyl)oxy]acetate

試薬・触媒・溶媒 2

HCID 94433Tetrabutylammonium hydrogen sulfate
触媒
HCID 1140Toluene溶媒

実験手順

To a solution of (3-{5-[2-(methoxymethyl)-2′-methylbiphenyl-4-yl]-1,2,4-oxadiazol-3-yl}phenyl)methanol, prepared as in example 159, step 1, (500 mg, 1.29 mmol) in toluene (10 mL) were added tert-butyl bromoacetate (215 μl, 1.45 mmol) and tetrabutylammonium hydrogen sulfate (45 mg, 0.13 mmol), followed by a 33% aqueous solution of sodium hydroxide (10 mL). The biphasic mixture was stirred strongly at RT for 45 minutes. The aqueous layer was removed. The organic layer was diluted with Et2O (20 mL) and washed with water (10 mL), then brine (10 mL). The organic layer was dried (MgSO4) and the solvents were removed under reduced pressure to give a yellow oil. This oil was purified by flash chromatography on silica (cHex/EtOAc) to give the title compound as a colorless oil. LC/MS (Method A): 501.4 (M+H)+. HPLC (Method A) Rt: 6.52 min (purity: 99.5%).

後処理

  1. customThe aqueous layer was removed
  2. additionThe organic layer was diluted with Et2O (20 mL)
  3. washwashed with water (10 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvents were removed under reduced pressure
  6. customto give a yellow oil
  7. customThis oil was purified by flash chromatography on silica (cHex/EtOAc)

出典と根拠

ORDレコード
ord-27087d266856426d9cabfebe563e8e3a
出典データセット
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08202865B2

反応ノート

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