Sodium Hydroxide → HCID 58043136, 화합물

HRID 1035170노트

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HRID 1035170 반응식
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([OH:18])[CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CS(O[CH:24]1[CH2:27][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:25]1)(=O)=O.[OH-].[Na+]>CN(C=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][C:10]=1[CH2:11][N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[O:18][CH:24]1[CH2:25][N:26]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:27]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 10753243Tert-butyl 3-(methanesulfonyloxy)azetidine-1-carboxylateHCID 580431463-Methoxy-4-(morpholinomethyl)phenol

생성물 1

HCID 58043136HCID 58043136, 화합물수율 105.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매3회

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온도
80 °C

실험 절차

A mixture of NaH (55-65% disp. in oil, 0.30 g, 6.88 mmol) in dry DMF (5 mL) under nitrogen was cooled by a water-bath. A solution of 7A (1.17 g, 5.24 mmol) in DMF (10 mL) was added drop-wise over 15 minutes. The mixture was stirred for one h and then tert-butyl 3-[(methylsulfonyl)oxy]azetidine-1-carboxylate (1.7 g, 6.77 mmol) in DMF (10 mL) was added. The mixture was heated to 80° C. for 3 days and then cooled to RT. Water and some aqueous NaOH were added and the mixture was extracted three times with EtOAc. The combined organic solutions were dried (MgSO4) and evaporated. The residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent. There was obtained 2.1 g (104%) of 7B as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 1.45 (s, 9H), 2.39-2.56 (m, 4H), 3.48 (s, 2H), 3.65-3.75 (m, 4H), 3.79 (s, 3H), 3.95-4.04 (m, 2H), 4.23-4.33 (m, 2H), 4.82-4.91 (m, 1H), 6.19 (d, 1H), 6.38 (s, 1H), 7.21 (d, 1H).

후처리

  1. temperaturewas cooled by a water-bath
  2. temperaturecooled to RT
  3. extractionthe mixture was extracted three times with EtOAc
  4. dry with materialThe combined organic solutions were dried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on SiO2 using 5% triethylamine in EtOAc as eluent

출처 및 근거

ORD 기록
ord-c778325494ed4aeab2275a5d00a2f54c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546375B2

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