Acetic Acid → HCID 178452510、化合物

HRID 1751614ノート

反応式

HRID 1751614 の反応式
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Br:12])=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:13][C:14]([C@@H:16]1[C@H:21]2[CH2:22][C@H:18]([CH2:19][CH2:20]2)[N:17]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=O.CC(O)=O.[OH-].[Na+]>C(OCC)(=O)C>[Br:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]1[NH:1][C:14]([C@@H:16]3[C@H:21]4[CH2:22][C@H:18]([CH2:19][CH2:20]4)[N:17]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[N:13][C:3]=1[CH:4]=[CH:5]2

参加物

5

反応物 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 86708790(1S,3S,4R)-tert-butyl 3-(1-amino-6-bromonaphthalen-2-ylcarbamoyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate

生成物 1

HCID 178452510HCID 178452510、化合物収率 93.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

(1S,3S,4R)-tert-butyl 3-(1-amino-6-bromonaphthalen-2-ylcarbamoyl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (2.01 g, 4.36 mmol) was suspended in AcOH (8.73 mL, 152.7 mmol) and placed in a preheated 50° C. oil bath. The suspension was let stir at 50° C. for 4 hours and at room temperature for 14 hours. Upon completion, the reaction mixture was diluted with ethyl acetate and aqueous NaOH (6M, 25.4 mL, 152.7 mmol) was added slowly with stirring. The layers were separated and the aqueous layer was back extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The resulting oil was purified by normal phase chromatography (30-55-100% ethyl acetate (5% MeOH) in hexanes) to give (1S,3S,4R)-tert-butyl 3-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylate (1.8 g, 93%). LCMS-ESI+: calc'd for C22H24BrN3O2: 441.11 (M+); Found: 442.7 (M+H+).

後処理

  1. customplaced in a preheated 50° C.
  2. additionwas added slowly
  3. stirringwith stirring
  4. customThe layers were separated
  5. extractionthe aqueous layer was back extracted with ethyl acetate twice
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting oil was purified by normal phase chromatography (30-55-100% ethyl acetate (5% MeOH) in hexanes)

出典と根拠

ORDレコード
ord-bdf5059cfacb4fd4bc156d2caed49e86
出典データセット
uspto-grants-2015_10
特許番号
US09156823B2

反応ノート

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