(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acid → 3-(1,3-Dioxolan-2-yl)propyl 4-(5-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)-1,2,4-oxadiazol-3-yl)benzoate

HRID 332710노트

반응식

HRID 332710 반응식
[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH2:14][C:15](O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:27][N:28]=[C:29]([C:31]1[CH:47]=[CH:46][C:34]([C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]2[O:45][CH2:44][CH2:43][O:42]2)=[O:36])=[CH:33][CH:32]=1)[NH2:30]>C(#N)C.N1C=CC=CC=1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([NH:8][CH:9]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:10]1[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=1)[O:13][CH2:14][C:15]1[O:27][N:28]=[C:29]([C:31]2[CH:32]=[CH:33][C:34]([C:35]([O:37][CH2:38][CH2:39][CH2:40][CH:41]3[O:42][CH2:43][CH2:44][O:45]3)=[O:36])=[CH:46][CH:47]=2)[N:30]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

6

반응물 2

HCID 71093126(3-(((tert-Butoxycarbonyl)amino)(phenyl)methyl)phenoxy)acetic acidHCID 866769173-(1,3-Dioxolan-2-yl)propyl 4-(N'-hydroxycarbamimidoyl)benzoate

생성물 1

HCID 710933303-(1,3-Dioxolan-2-yl)propyl 4-(5-((3-(((tert-butoxycarbonyl)amino)(phenyl)-methyl)phenoxy)methyl)-1,2,4-oxadiazol-3-yl)benzoate

시약·촉매·용매 3

HCID 1049Pyridine용매HCID 6342Acetonitrile용매HCID 57417360Sodium chloride; water용매

실험 절차

To a solution of 2-(3-(((tert-butoxycarbonyl)amino)(phenyl)methyl)phenoxy)-acetic acid (0.087 g. 0.34 mmol) and 3-(1,3-dioxolan-2-yl)propyl 4-(N′-hydroxy-carbamimidoyl)benzoate (0.10 g, 0.28 mmol) in acetonitrile (1 mL), was added 1-ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (0.087 g, 0.42 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with pyridine 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 sulfate, and the solvent evaporated at reduced pressure. The material was used directly in the next step without further purification (0.142 g, 87%).

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 sulfate
  4. customthe solvent evaporated at reduced pressure
  5. customThe material was used directly in the next step without further purification (0.142 g, 87%)

출처 및 근거

ORD 기록
ord-520e471813b34074baff470229cc5986
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08877774B2

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