alpha-Chlorohydrin, (+)- → HCID 59392504, 화합물

HRID 2065915노트

반응식

HRID 2065915 반응식
[CH2:1]([C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH2:24][CH3:25])[CH:17]=3)[N:12]=2)[CH:6]=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2].Cl[CH2:27][C@@H:28]([OH:31])[CH2:29][OH:30]>C(O)(C)C.[OH-].[Na+].CC(=O)OCC>[CH2:1]([C:3]1[CH:4]=[C:5]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[C:20]([CH3:22])[C:19]([O:23][CH2:27][C@@H:28]([OH:31])[CH2:29][OH:30])=[C:18]([CH2:24][CH3:25])[CH:17]=3)[N:12]=2)[CH:6]=[N:7][C:8]=1[CH2:9][CH3:10])[CH3:2]

참가 물질

6

반응물 2

HCID 148904alpha-Chlorohydrin, (+)-2회HCID 136170273HCID 136170273, 화합물

생성물 1

HCID 59392504HCID 59392504, 화합물수율 11.5%

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenol (100 mg, 0.296 mmol) in isopropanol (10 mL) and 3 N aq. NaOH (3 mL), (S)-3-chloro-1,2-propanediol (98 mg, 0.89 mmol) is added. The mixture is stirred at 60° C. for 24 h before another portion of (S)-3-chloro-1,2-propanediol (98 mg, 0.89 mmol) is added. Stirring is continued at 60° C. for 2 days. The mixture is diluted with EA and washed with sat. aq. NaHCO3 solution. The org. extract is dried over MgSO4, filtered and evaporated. The crude product is purified by chromatography on prep. TLC plates with EA-heptane to give (S)-3-{4-[5-(5,6-diethyl-pyridin-3-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol (14 mg) as a red oil; LC-MS: tR=0.93 min, [M+1]+=412.16.

후처리

  1. additionis added
  2. washwashed with sat. aq. NaHCO3 solution
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by chromatography on prep

출처 및 근거

ORD 기록
ord-be66c2f7874947428716cb5b866a8d1e
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08288554B2

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