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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
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HRID 1393483 반응식
[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
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7

반응물 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

생성물 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 ester수율 65%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-2ba3424effd0450ea54c95ca0f5cc2fa
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07345070B2

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