(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acid → Tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

HRID 332697노트

반응식

HRID 332697 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][C:7]1[CH:16]=[CH:15][C:10]([C:11](=[N:13][OH:14])[NH2:12])=[CH:9][CH:8]=1.[C:17]([O:21][C:22]([NH:24][CH:25]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[O:29][CH2:30][C:31](O)=O)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(#N)C.N1C=CC=CC=1.[Cl-].[Na+].O>[C:17]([O:21][C:22](=[O:23])[NH:24][CH:25]([C:26]1[CH:36]=[CH:35][CH:34]=[C:28]([O:29][CH2:30][C:31]2[O:14][N:13]=[C:11]([C:10]3[CH:15]=[CH:16][C:7]([CH2:6][CH:2]4[O:3][CH2:4][CH2:5][O:1]4)=[CH:8][CH:9]=3)[N:12]=2)[CH:27]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([CH3:20])([CH3:19])[CH3:18]

참가 물질

6

반응물 2

HCID 71093126(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acidHCID 866769114-((1,3-Dioxolan-2-yl)methyl)-N'-hydroxybenzimidamide

생성물 1

HCID 71113095Tert-butyl((3-((3-(4-((1,3-dioxolan-2-yl)methyl)phenyl)-1,2,4-oxadiazol-5-yl)methoxy)phenyl)(phenyl)methyl)carbamate

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6342Acetonitrile용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 4-((1,3-dioxolan-2-yl)methyl)-N′-hydroxybenzimidamide (0.747 g, 3.35 mmol) and 2-(3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)-acetic acid (Example 59 Step 2, 1.0 g, 2.79 mmol)) in acetonitrile (5 mL), was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.8 g, 4.18 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with pyridine (1 mL) and heated at 150° C. for 30 minutes in a microwave. The reaction was diluted with saturated brine and extracted with ethyl acetate (×3). The combined organic fractions were dried with magnesium sulphate, and the solvent evaporated at reduced pressure. Material used directly in the next step without further purification (1.01 g, 65%).

후처리

  1. temperatureheated at 150° C. for 30 minutes in a microwave
  2. extractionextracted with ethyl acetate (×3)
  3. dry with materialThe combined organic fractions were dried with magnesium sulphate
  4. customthe solvent evaporated at reduced pressure
  5. customMaterial used directly in the next step without further purification (1.01 g, 65%)

출처 및 근거

ORD 기록
ord-f4c39570920442a9b805b54aa1c1ac57
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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