Acetic Acid → HCID 44251674、化合物

HRID 76955ノート

反応式

HRID 76955 の反応式
[CH2:1]([N:8]([CH2:10][C:11]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15][C:14]([NH:23][CH3:24])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:33](B)#N.[Na].C(O)(=O)C>C(#N)C>[CH2:1]([N:8]([CH2:10][C:11]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:15][C:14]([N:23]([CH3:33])[CH3:24])([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]1)[CH3:9])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 68631306HCID 68631306、化合物HCID 101953985CID 101953985

生成物 1

HCID 44251674HCID 44251674、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A solution of the title compound from step 10 (diastereomer mixture) (0.350 g, 0.878 mmol) and formalin (1.23 mL, 37% aqueous solution) in acetonitrile (15 mL) was mixed in portions with sodium cyanoboron hydride (0.250 g, 3.86 mmol) and stirred for 45 min at room temperature. Conc. acetic acid was then added until a neutral reaction occurred and the mixture was subsequently stirred for 45 min at room temperature. For work up the solvent was removed in a vacuum, the residue taken up in 2N NaOH (40 mL) and then extracted with ether (3×40 mL). The organic solution was dried over Na2SO4, filtered and concentrated to low volume in a vacuum. The remaining residue was purified by Chromatotron and with cyclohexane/ethyl acetate 1:1. Separation of the diastereomers could not be achieved.

後処理

  1. stirringthe mixture was subsequently stirred for 45 min at room temperature
  2. customFor work up the solvent was removed in a vacuum
  3. extractionextracted with ether (3×40 mL)
  4. dry with materialThe organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to low volume in a vacuum
  7. customThe remaining residue was purified by Chromatotron and with cyclohexane/ethyl acetate 1:1
  8. customSeparation of the diastereomers could not

出典と根拠

ORDレコード
ord-0b626e7fa1cb4d45b450167a02c3121c
出典データセット
uspto-grants-2014_09
特許番号
US08835689B2

反応ノート

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