4-Azidophenacyl bromide → 2-Amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester

HRID 1468568ノート

反応式

HRID 1468568 の反応式
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11]Br)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:14]([NH:21][C:22]([NH2:24])=[NH:23])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C>[C:17]([O:16][C:14]([N:21]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=2)=[CH:11][N:23]=[C:22]1[NH2:24])=[O:15])([CH3:20])([CH3:18])[CH3:19]

参加物

4

反応物 2

HCID 926274-Azidophenacyl bromideHCID 178454308HCID 178454308、化合物

生成物 1

HCID 579314382-Amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester収率 98.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(4-azidophenyl)-2-bromoethanone (1.50 g, 6.24 mmol) in anhydrous DMF (20 mL) was added Boc-guanidine (3.00 g, 18.7 mmol). The reaction was stirred at ambient temperature for 48 hours upon which the mixture was partitioned between EtOAc (150 mL) and water (75 mL). The organic layer was successively washed with water (3×50 mL) and brine (2×50 mL) before being dried (Na2SO4) and evaporated to dryness. The resulting crude oil was purified via flash column chromatography (10-50% EtOAc/Hexanes) to obtain the target 2-amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester (1.84 g, 58%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 7.77 (d, 2H, J=8.1 Hz), 7.36 (s, 1H), 7.10 (dd, 2H, J=0.9, 8.1 Hz), 6.61 (br s, 2H), 1.58 (s, 9H); 13C NMR (75 MHz, DMSO-d6) δ 150.4, 148.9, 137.6, 136.2, 130.5, 126.2, 119.1, 106.2, 84.7, 27.5; HRMS (ESI) calcd for C8H6BrN3O (M+) 300.1335. found 300.1329.

後処理

  1. customwas partitioned between EtOAc (150 mL) and water (75 mL)
  2. washThe organic layer was successively washed with water (3×50 mL) and brine (2×50 mL)
  3. dry with materialbefore being dried (Na2SO4)
  4. customevaporated to dryness
  5. customThe resulting crude oil was purified via flash column chromatography (10-50% EtOAc/Hexanes)

出典と根拠

ORDレコード
ord-95db2e1efe9e4d00ad35b7d51f44c9c1
出典データセット
uspto-grants-2015_04
特許番号
US09005643B2

反応ノート

読み込み中…