Acetic Acid → 1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

HRID 1015532노트

반응식

HRID 1015532 반응식
[OH-].[Na+].BrBr.Br[O-].[N:7]1([CH2:12][C:13]23[CH2:21][CH:17]4[CH2:18][CH:19]([CH2:20]2)[C:15]([C:22](=[O:24])C)([CH2:16]4)[CH2:14]3)[CH:11]=[N:10][CH:9]=[N:8]1.CC(O)=[O:27]>O1CCOCC1.O>[N:7]1([CH2:12][C:13]23[CH2:21][CH:17]4[CH2:18][CH:19]([CH2:20]2)[C:15]([C:22]([OH:24])=[O:27])([CH2:16]4)[CH2:14]3)[CH:11]=[N:10][CH:9]=[N:8]1

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 5460626HypobromiteHCID 670178781-[1-(1H-1,2,4-triazol-1-ylmethyl) tricyclo[3.3.1.03,7]non-3-yl]ethanone

생성물 1

HCID 673003701-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid수율 75%

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매2회

실험 절차

To a stirred solution of NaOH (1.75 g, 43.8 mmol), H2O (14.6 mL) and 1,4 dioxane (2 mL) at ice bath temperature was added Br2 (0.8 mL, 16.4 mmol) and the mixture was stirred for 5 minutes. The resulting hypobromite solution was added drop-wise to a stirred solution of 1-[1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]non-3-yl]ethanone (0.7 g, 2.92 mmol) in 1,4-dioxane (4 mL) at ice bath temperature. The reaction mixture was gradually warmed to room temperature and stirred for 1 h. Then it was cooled to ice bath temperature and quenched by adding AcOH (3.9 mL, 65.7 mmol). The crude reaction mixture was diluted with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over Na2SO4, and the solvent was removed under reduced pressure to obtain 1-(1H-1,2,4-triazol-1-ylmethyl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (0.54 g) in 75% yield as an off-white solid. M.R: 230-235° C. m/z (M+1) 248. IR cm−1 3436, 3102, 2924, 2511, 1937, 1689, 1523, 1308, 1137, 979, 732. 1H NMR (CD3OD) 300 MHz δ 8.43 (s, 1H), 7.9 (s, 1H), 4.17 (s, 2H), 2.70-2.62 (m, 1H), 2.40-2.33 (m, 1H), 2.06-1.95 (m, 2H), 1.84-1.1.43 (m, 8H).

후처리

  1. stirringstirred for 1 h
  2. temperatureThen it was cooled to ice bath temperature
  3. customquenched
  4. customThe crude reaction mixture
  5. extractionextracted with EtOAc
  6. washThe combined organic layer was washed with brine
  7. dry with materialdried over Na2SO4
  8. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-d68c1c91f1fc4f84ae80d4e49d07d3af
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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