Ammonium Chloride → HCID 21879615、化合物

HRID 72076

反応式

HRID 72076 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]2.C([Li])CCC.[CH:20]1[N:24]=[CH:23][N:22]2[CH2:25][CH2:26][C:27](=[O:28])[C:21]=12.[Cl-].[NH4+]>C1COCC1.CCCCCC.C(OCC)(=O)C>[OH:28][C:27]1([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH:8]=[C:7]([C:12]([OH:14])=[O:13])[CH:6]=[CH:5]3)[C:21]2[N:22]([CH:23]=[N:24][CH:20]=2)[CH2:25][CH2:26]1

参加物

8

反応物 4

HCID 25517Ammonium ChlorideHCID 45498526-Bromo-2-naphthalenecarboxylic acidHCID 111709605,6-Dihydropyrrolo[1,2-c]imidazol-7-oneHCID 178418339Butyllithium

生成物 1

HCID 21879615HCID 21879615、化合物収率 12.2%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-100 °C

実験手順

6-Bromo-2-naphthoic acid (1.51 g) was dissolved in dry THF (50 ml), and cooled to −100° C. in a liquid nitrogen/diethyl ether bath. Under stirring a solution (1.6M; 7.88 ml) of n-butyllithium in hexane was added dropwise at −95° C. or below over 5 min. After stirring at −100° C. for 30 min and at −80° C. for 10 min, the mixture was cooled to −100° C. again. A solution of 5,6-dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (0.61 g) in dry THF (11 ml) was added dropwise at −90° C. or below over 5 min. After stirring at the same temperature for 30 min, the temperature was raised to −70° C. over 30 min, and saturated aqueous ammonium chloride solution (25 ml) was added to quench the reaction. After stirring for 10 min, ethyl acetate (50 ml) was added to partition the solution. The organic layer was removed and the aqueous layer was concentrated to dryness. The obtained residue was purified by flash column chromatography, and the object fraction was dissolved in methanol. This solution was concentrated, ether was added to the precipitated powder and the powder was collected by filtration and dried. The title compound (180 mg) was obtained as a colorless powder. The mother liquor was concentrated to give a residue (449 mg) containing the title compound.

後処理

  1. additionwas added dropwise at −95° C. or below over 5 min
  2. temperaturethe mixture was cooled to −100° C. again
  3. stirringAfter stirring at the same temperature for 30 min
  4. temperaturethe temperature was raised to −70° C. over 30 min
  5. customto quench
  6. customthe reaction
  7. stirringAfter stirring for 10 min
  8. customto partition the solution
  9. customThe organic layer was removed
  10. concentrationthe aqueous layer was concentrated to dryness
  11. customThe obtained residue was purified by flash column chromatography
  12. dissolutionthe object fraction was dissolved in methanol
  13. concentrationThis solution was concentrated
  14. additionether was added to the precipitated powder
  15. filtrationthe powder was collected by filtration
  16. customdried

出典と根拠

ORDレコード
ord-eee504e596d047aa96630c28e07c86e5
出典データセット
uspto-grants-2014_09
特許番号
US08828429B2

関連ノート

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