Sodium Hydroxide → 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic Acid

HRID 585291노트

반응식

HRID 585291 반응식
[OH-].[Na+].C([O:5][C:6](=[O:43])[C:7]([CH3:42])([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]2[CH:41]=[CH:40][S:39][CH:38]=2)[CH:32]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)C.C(OC(=O)C(C)(OC1C=CC=CC=1)CC1C=CC(OCCC2N=C(C3CCCCC3)OC=2C)=CC=1)C>C(O)C>[CH:24]1([C:20]2[O:21][C:22]([CH3:23])=[C:18]([CH2:17][CH2:16][O:15][C:12]3[CH:11]=[CH:10][C:9]([CH2:8][C:7]([CH3:42])([O:30][C:31]4[CH:36]=[CH:35][CH:34]=[C:33]([C:37]5[CH:41]=[CH:40][S:39][CH:38]=5)[CH:32]=4)[C:6]([OH:43])=[O:5])=[CH:14][CH:13]=3)[N:19]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 208231423-(4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic acid ethyl esterHCID 208231432-Methyl-3-(4-{2-[5-methyl-2-cyclohexyl-oxazol-4-yl]-ethoxy}-phenyl)-2-phenoxypropionic Acid Ethyl Ester

생성물 1

HCID 223399763-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic Acid

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

5N NaOH (0.5 mL) was added to a solution of 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy]-phenyl}-2-methyl-2-(3-thiophen-3-yl-phenoxy)-propionic acid ethyl ester and 3-{4-[2-(2-Cyclohexyl-5-methyl-oxazol-4-yl)-ethoxy-]-phenyl}-2-methyl-2-phenoxy-propionic acid ethyl ester in ethanol (4 mL). The resultant mixture was refluxed under an atmosphere of nitrogen for 2 h, then cooled to ambient temperature. The reaction mixture was concentrated in vacuo, diluted with 1N HCl, and extracted with CH2Cl2. The organic layer was dried through a Varian ChemElut cartridge, concentrated in vacuo, and purified by LCMS. 1H NMR (400 MHz, CDCl3): δ 7.39-7.26 (m, 5H), 7.17 (d, 2H, J=8.60 Hz), 7.11-7.10 (m, 1H), 6.82-6.80 (m, 1H), 6.78 (d, 2H, J=8.60 Hz), 4.11 (t, 2H, J=6.26 Hz), 3.25 (d, 1H, J=14.08 Hz), 3.13 (d, 1H, J=14.08 Hz), 2.93 (t, 2H, J=6.26 Hz), 2.87-2.81 (m, 1H), 2.28 (s, 3H), 1.99 (d, 2H, J=12.51 Hz), 1.77 (d, 2H, J=12.51), 1.67 (d, 2H, J=12.51), 1.57-1.46 (m, 2H), 1.45 (s, 3H), 1.37-1.19 (m, 2H). MS [ES+] m/z exact mass calcd for C32H36NO5S 546.2314, found 546.2308.

후처리

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with 1N HCl
  3. extractionextracted with CH2Cl2
  4. customThe organic layer was dried through a Varian ChemElut cartridge
  5. concentrationconcentrated in vacuo
  6. custompurified by LCMS

출처 및 근거

ORD 기록
ord-6bda5e6263014371b7c18909d7870502
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06930120B2

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