Triethylamine → tert-Butyl (6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

HRID 1270406ノート

反応式

HRID 1270406 の反応式
N[CH:2]([NH:10][C:11]1[CH:19]=[C:18]([Br:20])[CH:17]=[CH:16][C:12]=1C(O)=O)[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)CC)C>C1(C)C=CC=CC=1>[Br:20][C:18]1[CH:17]=[CH:16][C:12]2[NH:40][C:43](=[O:28])[N:10]([CH2:2][C:3]([O:5][C:6]([CH3:7])([CH3:8])[CH3:9])=[O:4])[C:11]=2[CH:19]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 184493622-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid

生成物 1

HCID 86607790tert-Butyl (6-bromo-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)acetate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

2-[(1-Amino-2-tert-butoxy-2-oxoethyl)amino]-4-bromobenzoic acid from Step C (2.72 g, 8.24 mmol), diphenylphosphoryl azide (2.1 mL, 9.9 mmol), and triethylamine (1.4 mL, 9.9 mmol) were dissolved in toluene (80 mL) and heated at 100° C. for 1 h. The cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=327 (M+1).

後処理

  1. customThe cooled mixture was partitioned between EtOAc (200 mL) and water (100 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography
  6. washeluting with a gradient of hexane

出典と根拠

ORDレコード
ord-f7783615d34c40889adc1af8c9f100c0
出典データセット
uspto-grants-2007_04
特許番号
US07202251B2

反応ノート

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