Potassium Carbonate → Tert-butyl ((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate

HRID 445399노트

반응식

HRID 445399 반응식
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[S:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:12][N:13]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[F:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br>CN(C)C=O>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][C:9]1[S:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]([O:20][CH2:32][C:31]3[CH:34]=[CH:35][CH:36]=[C:29]([F:28])[CH:30]=3)=[CH:18][CH:19]=2)=[N:12][N:13]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 680073-Fluorobenzyl bromideHCID 136340687Tert-butyl ((5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate

생성물 1

HCID 86663647Tert-butyl ((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-(5-(aminomethyl)-1,3,4-thiadiazol-2-yl)phenol (1 g, 3.5 mmol) in methanol (9 mL) containing NaHCO3 (1.2 g, 13.9 mmol) and di-t-butyldicarbonate (Boc2O; 1.5 g, 7.0 mmol) was stirred for 5 h. The resulting mixture was filtered and the filtrate concentrated. The residue was dissolved in CH2Cl2 (48 mL) and treated with 0.5 M NaOCH3 in methanol (8.3 mL). After stirring at room temperature for 1 h, the volatiles were removed under vacuum to yield tert-butyl ((5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate. To a solution of tert-butyl((5-(4-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate (1.01 g, 2.89 mmol), dimethylformamide (16 mL) and potassium carbonate (1.36 g, 9.86 mmol) was added 3-fluorobenzylbromide (0.61 mL, 4.93 mmol), and the mixture was stirred at room temperature overnight. After 24 h, the resulting mixture was filtered and the filtrate was concentrated. The residue was purified by chromatography (silica gel, heptane:EtOAc) to yield tert-butyl((5-(4-((3-fluorobenzyl)oxy)phenyl)-1,3,4-thiadiazol-2-yl)methyl)carbamate. 1H NMR (400 MHz, CDCl3) δ 7.87-7.92 (m, 2H), 7.33-7.42 (m, 1H), 7.14-7.23 (m, 2H), 7.01-7.08 (m, 3H), 5.13 (s, 2H), 4.68-4.77 (m, 2H), and 1.48 (s, 9H); MS (ES+) 416 (M+1).

후처리

  1. waitAfter 24 h
  2. filtrationthe resulting mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by chromatography (silica gel, heptane:EtOAc)

출처 및 근거

ORD 기록
ord-6e64e49caced4f94b996330ea8322111
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476302B2

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