Acetic Acid → HCID 178452510, 화합물

HRID 1751614노트

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HRID 1751614 반응식
[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

참가 물질

5

반응물 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

생성물 1

HCID 178452510HCID 178452510, 화합물수율 93.3%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

(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+).

후처리

  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)

출처 및 근거

ORD 기록
ord-bdf5059cfacb4fd4bc156d2caed49e86
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156823B2

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