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Potassium Hydroxide → 2-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester

HRID 352442
ノート
印刷プレビュー

反応式

HRID 352442 の反応式
[OH-].[K+].[C:3]([O:7][C:8](=[O:31])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42]Br)[CH3:33]>CS(C)=O>[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][N:9]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:14][CH:15]=1)[CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 14797Potassium HydroxideHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 69486797{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester

生成物 1

HCID 694866072-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester収率 94%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒
2 回

実験手順

To a suspension of 3.41 g of powdered KOH in 110 ml of DMSO was added at 22° C. 6.00 g of {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester and the suspension was stirred for 25 min. A solution of 7.40 g of 2-bromomethyl-benzoic acid ethyl ester in 10 ml of DMSO was added slowly keeping the temperature at 15-20° C. and stirring was continued at 22° C. for 2.5 h. The dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt, the organic layer was washed with saturated aqueous NH4Cl and water, dried and evaporated. The residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 7.96 g of the title compound as a pale yellow oil. MS: (M+H)+ 557.3.

後処理

  1. additionwas added at 22° C
  2. customat 15-20° C.
  3. customThe dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt
  4. washthe organic layer was washed with saturated aqueous NH4Cl and water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1)

出典と根拠

ORDレコード
ord-916188e7e8ba4087be5d272a3211af8f
出典データセット
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06747049B2

反応ノート

読み込み中…

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