Cesium carbonate → (2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester

HRID 11707노트

반응식

HRID 11707 반응식
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][C:8]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:12][C@H:11]2[CH2:24][C:25]([NH2:27])=[O:26])=[O:9])=[C:4]([OH:30])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>O1CCOCC1>[C:42]([O:41][C:39](=[O:40])[CH2:38][O:30][C:4]1[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]=1[O:6][CH2:7][C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[CH2:24][C:25](=[O:26])[NH2:27])=[O:9])([CH3:45])([CH3:44])[CH3:43]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 69655726(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide

생성물 1

HCID 69656159(2-{2-[(2R)-2-carbamoylmethyl-4-(4-fluoro-benzyl)-piperazin-1-yl]-2-oxo-ethoxy}-5-chloro-phenoxy)-acetic Acid tert-butyl Ester수율 87.5%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

(2R)-2-[1-[(4-Chloro-2-hydroxy-phenoxy)-acetyl]-4-(4-fluoro-benzyl)-piperazin-2-yl]-acetamide (0.070 g, 0.16 mmol), cesium carbonate (0.078 g, 0.24 mmol) and tert-butyl bromoacetate (0.038 g, 0.028 mL, 0.193 mmol) were stirred in dioxane (2 mL). After 2.5 days, the solution was filtered, concentrated and chromatographed on silica gel to yield the title compound as a white solid (0.077 g).

후처리

  1. filtrationthe solution was filtered
  2. concentrationconcentrated
  3. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-cf0e8160df2f4b5284c3b3935cb1a9cb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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