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

HRID 445399ノート

反応式

HRID 445399 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-6e64e49caced4f94b996330ea8322111
出典データセット
uspto-grants-2013_07
特許番号
US08476302B2

反応ノート

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