Dichloromethane → 3-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

HRID 1628160노트

반응식

HRID 1628160 반응식
[CH2:1]([O:8][C:9](=[O:29])[CH:10]([O:26][CH2:27][CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][C:31]1[O:35][C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:33][C:32]=1[CH2:42][C:43](O)=[O:44].C(Cl)Cl>CCCCCCC.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:29])[CH:10]([O:26][CH2:27][CH3:28])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:43](=[O:44])[CH2:42][C:32]2[N:33]=[C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:35][C:31]=2[CH3:30])=[C:14]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 27751395-Methyl-2-phenyl-4-oxazoleacetic acidHCID 668645693-(3-Benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester

생성물 1

HCID 668644523-{3-Benzyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-acetoxy]-phenyl}-2-ethoxy-propionic acid benzyl ester

시약·촉매·용매 1

HCID 21899848Ethylacetate heptane용매

실험 절차

To a solution of 3-(3-benzyl-4-hydroxy-phenyl)-2-ethoxy-propionic acid benzyl ester (45 mg, 0.11 mol) and (5-methyl-2-phenyl-oxazol-4-yl)-acetic acid (25 mg, 0.11 mmol) in dry DCM (2.0 mL) first DMAP (2.8 mg, 0.02 mmol) and then EDCxHCl (26.5 mg, 0.13 mmol) was added and the mixture was stirred under nitrogen atmosphere at room temperature for 17 h. The solvent was removed under vacuo and the product was isolated out of the remaining oil by column chromatography using n-heptane/EtOAc (4:1) as the eluent. The title compound was obtained as an oil (56.1 mg, 82.6%). 1H NMR (400 MHz, CDCl3): δ 7.95 (m, 2H), 7.40 (m, 2H), 7.32 (m, 2H), 7.25 (m, 2H), 6.98-67.20 (m, 10H), 5.08, (d, 2H), 3.97 (t, 1H), 3.85 (s, 2H), 3.70 (s, 2H), 3.55 (m, 1H), 3.28 (m, 1H), 2.93 (d, 2H), 2.32 (s, 3H), 1.1 (t, 3H).

후처리

  1. customThe solvent was removed under vacuo
  2. customthe product was isolated out of the remaining oil by column chromatography

출처 및 근거

ORD 기록
ord-23cd6723e2234c72895ac2e856d02c8e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785681B2

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