Hydrochloric Acid → 3-[1-[4-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid

HRID 350036ノート

反応式

HRID 350036 の反応式
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]2[CH:11]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])=[CH:8]2)=[CH:4][CH:3]=1.Cl[CH2:28][C:29]1[N:30]=[C:31]([C:35]2[O:36][CH:37]=[CH:38][CH:39]=2)[O:32][C:33]=1[CH3:34].C(=O)([O-])[O-].[K+].[K+].Cl.[OH-].[Na+]>C(O)C.O1CCCC1.CN(C)C=O>[O:36]1[CH:37]=[CH:38][CH:39]=[C:35]1[C:31]1[O:32][C:33]([CH3:34])=[C:29]([CH2:28][O:1][C:2]2[CH:26]=[CH:25][C:5]([CH2:6][N:7]3[CH:11]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=4)[C:9]([CH2:18][CH2:19][C:20]([OH:22])=[O:21])=[CH:8]3)=[CH:4][CH:3]=2)[N:30]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazoleHCID 23024736Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate

生成物 1

HCID 694244913-[1-[4-[2-(2-Furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid収率 73.1%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (1.01 g), 4-chloromethyl-2-(2-furyl)-5-methyloxazole (0.75 g), potassium carbonate (0.63 g) and N,N-dimethylformamide (15 ml) was stirred at room temperature overnight. The reaction mixture was poured into dilute hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), and then concentrated. The residue was subjected to silica gel column chromatography, and an oily substance was obtained from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). A mixture of the oily substance obtained, 1N aqueous sodium hydroxide solution (6 ml), tetrahydrofuran (5 ml) and ethanol (10 ml) was stirred at room temperature for 3 hours and the organic solvent was removed under reduced pressure. After adding water, the residue was acidified by adding 1N hydrochloric acid. The colorless crystals obtained were collected by filtration to yield 3-[1-[4-[2-(2-furyl)-5-methyl-4-oxazolylmethoxy]benzyl]-4-phenyl-3-pyrrolyl]propionic acid (1.02 g, yield: 73%). This was recrystallized from ethyl acetate-hexane. Melting point: 86–87° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customan oily substance was obtained from the fraction
  6. washeluted with ethyl acetate-hexane (1:2, volume ratio)
  7. additionA mixture of the oily substance
  8. customobtained
  9. customthe organic solvent was removed under reduced pressure
  10. additionAfter adding water
  11. additionby adding 1N hydrochloric acid
  12. customThe colorless crystals obtained
  13. filtrationwere collected by filtration

出典と根拠

ORDレコード
ord-51c62b8def54402cb5337f729300586d
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

反応ノート

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