Hydrochloric Acid → HCID 178461482、化合物

HRID 2097678ノート

反応式

HRID 2097678 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:15]=[N:16][NH:17][C:18]=1[C:19]([O:21]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl.[CH3:27][C@H:28]1[C@H:36]([NH2:37])[CH2:35][C@H:31]2[C:32]([CH3:34])([CH3:33])[C@@H:29]1[CH2:30]2.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.[Cl-].[Na+].O.CN(C=O)C.CCOC(C)=O.C1COCC1.CO>[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[N:15]=[N:16][NH:17][C:18]=1[C:19]([NH:37][C@@H:36]1[CH2:35][C@H:31]2[CH2:30][C@@H:29]([C:32]2([CH3:34])[CH3:33])[C@H:28]1[CH3:27])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

12

反応物 6

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11744832(1R,2R,3R,5S)-2,6,6-Trimethylbicyclo[3.1.1]heptan-3-amineHCID 178470429HCID 178470429、化合物

生成物 1

HCID 178461482HCID 178461482、化合物

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 21899815MeOH tetrahydrofuran溶媒HCID 57417360Sodium chloride; water溶媒2 回

反応条件

温度
50 °C

実験手順

A solution of ester (9) (1.0 equiv) in 2.5:1 THF/MeOH (0.5 M) was treated with a solution of lithium hydroxide (3.0 equiv) in water (1.6 M), and the resulting mixture was stirred at 50° C. overnight, cooled to room temperature, acidified with 1M HCl, diluted with brine and extracted with AcOEt (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The pale yellow foam obtained was dissolved in dry DMF (0.4 M) and treated with (−)-isopinocampheyl amine (12) (1.0 equiv), followed by triethylamine (1.0 equiv) and HBTU (1.0 equiv). The resulting solution was stirred at rt for 1 h, diluted with brine and AcOEt. The layers were separated and the aqueous one was washed with brine (2×), 1M HCl and brine (2×), dried (MgSO4), filtered and concentrated under reduced pressure to provide 4-(2-phenoxyphenyl)-N-((1R,2R,3R,5R)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)-1H-1,2,3-triazole-5-carboxamide (13) as a pale yellow foam and was used without further purification.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with AcOEt (3×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe pale yellow foam obtained
  8. stirringThe resulting solution was stirred at rt for 1 h
  9. customThe layers were separated
  10. washthe aqueous one was washed with brine (2×), 1M HCl and brine (2×)
  11. dry with materialdried (MgSO4)
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ef10f19995b446e8b6b78aa0ab190155
出典データセット
uspto-grants-2013_05
特許番号
US08450350B2

反応ノート

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