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Methanol → 2-(2-Oxo-1,3-oxazinan-3-yl)acetic acid

HRID 1947741
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HRID 1947741 반응식
[O:1]=[C:2]1[N:7]([CH2:8][C:9]([O:11]C)=[O:10])[CH2:6][CH2:5][CH2:4][O:3]1.O.CO.[OH-].[Na+]>C1COCC1>[O:1]=[C:2]1[N:7]([CH2:8][C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][O:3]1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 77231409Methyl (2-oxo-1,3-oxazinan-3-yl)acetate

생성물 1

HCID 579076012-(2-Oxo-1,3-oxazinan-3-yl)acetic acid수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 0.068 g (0.39 mmol) of methyl (2-oxo-1,3-oxazinan-3-yl)acetate from step B above in 6 mL of THF and 2 mL of water and 2 mL of methanol was added 0.60 mL (1.2 mmol) of an aqueous 2.0 M sodium hydroxide solution. The resulting mixture was stirred at ambient temperature for 3 h and then evaporated in vacuo to remove the methanol and THF. The aqueous phase was acidified with a 2 N hydrochloric acid solution until a pH of 2 was achieved and then extracted with a 30% isopropyl alcohol in chloroform mixture (3×10 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound as an off-white solid (0.06 g, 99%). 1H NMR (CD3OD, 500 MHz) δ: 4.32 (t, J=5.4 Hz, 2H), 4.03 (s, 2H), 3.41 (t, J=6.2 Hz, 2H), 2.10-2.05 (m, 2H). LC-MS: m/z (ES) 160 (MH)+.

후처리

  1. customevaporated in vacuo
  2. customto remove the methanol and THF
  3. extractionextracted with a 30% isopropyl alcohol in chloroform mixture (3×10 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-d894a087fc024e76b7a606fabaf4a026
출처 데이터셋
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08399480B2

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