tert-Butanol → Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate

HRID 468898노트

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HRID 468898 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7](C(O)=O)[N:8]=[CH:9]2)=[CH:4][N:3]=1.[C:15]([OH:19])([CH3:18])([CH3:17])[CH3:16].C([N:23]([CH2:27]C)C(C)C)(C)C.C1C=CC([O:35]P(OC2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH:23][C:27](=[O:35])[O:19][C:15]([CH3:18])([CH3:17])[CH3:16])[N:8]=[CH:9]2)=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 6386tert-ButanolHCID 81531DiisopropylethylamineHCID 123414Diphenylphosphoryl azideHCID 866749707-Chloro-2,6-naphthyridine-3-carboxylic acid

생성물 1

HCID 86674971Tert-butyl 7-chloro-2,6-naphthyridin-3-ylcarbamate수율 83%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
110 °C

실험 절차

A mixture of 7-chloro-2,6-naphthyridine-3-carboxylic acid (360 mg, 1.8 mmol), tert-butyl alcohol (3.4 mL), N,N-diisopropylethylamine (1 mL, 5.6 mmol), and diphenylphosphonic azide (1.0 mL, 4.5 mmol) in toluene (6 mL) was heated at 110° C. for 1 hour. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (50 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane) to afford the title compound as a pale yellow solid (410 mg, 83%), which was used in the next step without further purification.

후처리

  1. customThe cooled reaction mixture
  2. washwashed with water (50 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto afford a residue that
  8. customwas purified by flash chromatography (silica, 12 g, ISCO, 0-60% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-48feea5f538b4a57a102398199b2ad1b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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