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

HRID 1270406노트

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HRID 1270406 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
100 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f7783615d34c40889adc1af8c9f100c0
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202251B2

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