Benzylethanolamine → HCID 178499151、化合物

HRID 535913ノート

反応式

HRID 535913 の反応式
[CH:1]([C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[CH2:19]([NH:26][CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[CH2:19]([N:26]([CH2:1][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([O:10][CH3:11])=[O:9])[CH2:27][CH2:28][OH:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 4348BenzylethanolamineHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 178499152Methyl 5-formyl-1H-imidazole-4-carboxylate

生成物 1

HCID 178499151HCID 178499151、化合物収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred suspension of Intermediate 1C (3.20 g, 20.76 mmol) in dry THF (180 mL) was added anhydrous Na2SO4 (14.48 g, 192 mmol) and N-benzylethanolamine (3.70 g, 24.47 mmol). The resulting mixture was stirred at room temperature under nitrogen for 1 hour. Sodium triacetoxyborohydride (6.37 g, 28.5 mmol) was added portion-wise and the resulting mixture was stirred under nitrogen for 48 hours. The resulting mixture was quenched with water and neutralized with saturated NaHCO3 solution. The mixture was extracted with DCM and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated. The crude mixture was purified using normal phase chromatography eluting with a 10-30% methanol/DCM gradient to provide Intermediate 1D as a white solid (5.80 g, 98%).

後処理

  1. stirringthe resulting mixture was stirred under nitrogen for 48 hours
  2. customThe resulting mixture was quenched with water and neutralized with saturated NaHCO3 solution
  3. extractionThe mixture was extracted with DCM
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified
  8. washeluting with a 10-30% methanol/DCM gradient

出典と根拠

ORDレコード
ord-3fca3f363a1e4466a5427b35c4124ebd
出典データセット
uspto-grants-2014_10
特許番号
US08859538B2

反応ノート

読み込み中…