Alendronic Acid → 4-Aminobenzamide

HRID 535209

반응식

HRID 535209 반응식
[CH2:1]([CH2:13]N)[CH2:2][C:3](P([O-])(O)=O)(P(O)(O)=O)[OH:4].[Na+:15].[OH-].[Na+].[N+:18]([C:21]1C=CC=[CH:26][C:22]=1C(Cl)=O)([O-])=O.[CH2:30]([CH2:42][NH2:43])[CH2:31][C:32]([P:38]([OH:41])([OH:40])=[O:39])([P:34]([OH:37])([OH:36])=[O:35])[OH:33]>O.C1COCC1>[NH2:18][C:21]1[CH:13]=[CH:1][C:2]([C:3]([NH2:43])=[O:4])=[CH:26][CH:22]=1.[CH2:30]([CH2:42][NH2:43])[CH2:31][C:32]([P:34]([O-:36])([OH:37])=[O:35])([P:38]([OH:41])([OH:40])=[O:39])[OH:33].[Na+:15]

참가 물질

8

반응물 4

HCID 2088Alendronic AcidHCID 118752-Nitrobenzoyl chlorideHCID 14798Sodium Hydroxide2회HCID 16760285Alendronate sodium anhydrous

생성물 2

HCID 760794-AminobenzamideHCID 16760285Alendronate sodium anhydrous

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

The 4-aminobenzamide of alendronate sodium was prepared as follows. In a 500 mL beaker, 54 g (166 mmol) of sodium alendronate was dissolved in 150 mL of DI water with a pH adjusted to 11 with concentrated NaOH. Nitrobenzoyl chloride, 28 g (150 mmol), dissolved in 100 mL of THF, was added dropwise into the aqueous alendronate solution. The pH was kept at 11 with additional NaOH solution during the addition. After the addition was complete, the solution was stirred for another 2 hours at room temperature. THF was removed in vacuo, and the pH of the solution was adjusted to 4. The resulting precipitate, which was collected by filtration at room temperature, was primarily nitrobenzoic acid and was discarded. The solution was kept at 4° C. overnight, and the resulting precipitate was collected by filtration, washed with DI water, and dried. The resulting solid weighted approximately 56 g (86%).

후처리

  1. additionAfter the addition
  2. customTHF was removed in vacuo
  3. filtrationThe resulting precipitate, which was collected by filtration at room temperature
  4. waitThe solution was kept at 4° C. overnight
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with DI water
  7. customdried

출처 및 근거

ORD 기록
ord-c85c51da5815432c804935d31ca0b10f
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08858695B2

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