Acetic Acid → HCID 44251674, 화합물

HRID 1477215노트

반응식

HRID 1477215 반응식
[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

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 68631306HCID 68631306, 화합물HCID 101953985CID 101953985

생성물 1

HCID 44251674HCID 44251674, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-257cd35917d4470b92b3c32149b40482
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09403767B2

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