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Methanol → 3-{5-[1-Hydroxy-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-methyl-2-phenoxy-propionic acid methyl ester

HRID 1393483
ノート
印刷プレビュー

反応式

HRID 1393483 の反応式
[CH3:1][O:2][C:3](=[O:35])[C:4]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:5][C:6]1[S:7][C:8]([C:11](=[O:26])[CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1.CO.[BH4-].[Na+].CCOC(C)=O>C1COCC1.CCCCCC>[CH3:1][O:2][C:3](=[O:35])[C:4]([CH3:34])([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:5][C:6]1[S:7][C:8]([CH:11]([OH:26])[CH2:12][CH2:13][C:14]2[N:15]=[C:16]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:17][C:18]=2[CH3:19])=[CH:9][CH:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 208231592-Methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propionyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester

生成物 1

HCID 208231613-{5-[1-Hydroxy-3-(5-methyl-2-phenyl-oxazol-4-yl)-propyl]-thiophen-2-yl}-2-methyl-2-phenoxy-propionic acid methyl ester収率 65%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A sample of 2-methyl-3-{5-[3-(5-methyl-2-phenyl-oxazol-4-yl)-propionyl]-thiophen-2-yl}-2-phenoxy-propionic acid methyl ester (1.00 g, 2.04 mmol) was dissolved in THF (40 mL) and MeOH (20 mL) and cooled to 0° C. Sodium borohydride (115 mg, 3.06 mmol) was added and allowed to stir at 0° C. for 45 min. The reaction was monitored by HPLC. Upon the completion of the reaction, the bulk of the solvent was removed in vacuo and water (40 mL) was added. The mixture was acidified with 6 N HCl (20 mL) and stirred for 30 min. This aqueous mixture was then extracted with CH2Cl2 (2×50 mL). The organic fractions were combined, dried over NaCl, and solvent removed in vacuo to give a crude oil. Flash chromatography (gradient 20% to 40% EtOAc in hexane) provided 650 mg (65%) of desired product: 1H NMR (400 MHz, CDCl3) δ 8.02 (d, 2 H), 7.47 (m, 3 H), 7.19 (m, 2 H), 6.96 (t, 1 H), 6.79 (m, 3 H), 6.68 (d, 2 H), 4.96 (m, 1 H), 3.72 (s, 3 H), 3.43 (d, 1 H), 3.29 (d, 1 H), 2.71 (m, 2 H), 2.30 (s, 3 H), 2.17 (m, 2 H), 1.42 (s, 3 H); MS (EI) 492.2 (M+H)+.

後処理

  1. customUpon the completion of the reaction
  2. customthe bulk of the solvent was removed in vacuo and water (40 mL)
  3. additionwas added
  4. stirringstirred for 30 min
  5. extractionThis aqueous mixture was then extracted with CH2Cl2 (2×50 mL)
  6. dry with materialdried over NaCl, and solvent
  7. customremoved in vacuo
  8. customto give a crude oil

出典と根拠

ORDレコード
ord-2ba3424effd0450ea54c95ca0f5cc2fa
出典データセット
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07345070B2

反応ノート

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