Benzyl Alcohol → N-(carbobenzyloxy)amino-3-methoxynaphthalene

HRID 78296

반응식

HRID 78296 반응식
[CH3:1][O:2][C:3]1[C:4](C(O)=O)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.CC[N:18]([CH2:21]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.[CH2:40]([OH:47])[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1(C)C=CC=CC=1>[C:21]([NH:18][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:3]([O:2][CH3:1])[CH:4]=1)([O:47][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:30]

참가 물질

6

반응물 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 701613-Methoxy-2-naphthoic acidHCID 199401P,P-Diphenylphosphinic azide

생성물 1

HCID 23023062N-(carbobenzyloxy)amino-3-methoxynaphthalene수율 100%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

A solution of 3-methoxy-2-naphthoic acid (3.36 g, 16.6 mmol) and Et3N (2.59 mL, 18.6 mmol) in anh toluene (70 mL) was stirred at room temp. for 15 min., then treated with a solution of DPPA (5.12 g, 18.6 mmol) in toluene (10 mL) via pipette. The resulting mixture was heated at 80° C. for 2 h. After cooling the mixture to room temp., benzyl alcohol (2.06 mL, 20 mmol) was added via syringe. The mixture was then warmed to 80° C. overnight. The resulting mixture was cooled to room temp., quenched with a 10% citric acid solution, and extracted with EtOAc (2×100 mL). The combined organic layers were washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by column chromatography (14% EtOAc/86% hexane) to give 2-(N-(carbobenzyloxy)amino-3-methoxynaphthalene as a pale yellow oil (5.1 g, 100%): 1H-NMR (DMSO-d6) δ 3.89 (s, 3H), 5.17 (s, 2H), 7.27-7.44 (m, 8H), 7.72-7.75 (m, 2H), 8.20 (s, 1H), 8.76 (s, 1H).

후처리

  1. temperatureAfter cooling the mixture to room temp.
  2. temperatureThe mixture was then warmed to 80° C. overnight
  3. temperatureThe resulting mixture was cooled to room temp.
  4. customquenched with a 10% citric acid solution
  5. extractionextracted with EtOAc (2×100 mL)
  6. washThe combined organic layers were washed with a saturated NaCl solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by column chromatography (14% EtOAc/86% hexane)

출처 및 근거

ORD 기록
ord-fdbf4b2d30004055afc47039e51a280d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841330B2

연결된 노트

불러오는 중…