Alendronic Acid → Sodium (4-(4-aminobenzenesulfonylamino)-1-hydroxybutane-1,1-diyl)bisphosphonate

HRID 630557

반응식

HRID 630557 반응식
[CH2:1]([CH2:13][NH2:14])[CH2:2][C:3]([P:9]([O-:12])([OH:11])=[O:10])([P:5]([OH:8])([OH:7])=[O:6])[OH:4].[Na+:15].[Na].[NH2:17]CCCC(P(=O)(O)O)(P(=O)(O)O)O.[OH-].[Na+].[N+]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[S:42](Cl)(=[O:44])=[O:43])([O-])=O>O1CCCC1.O>[NH2:17][C:40]1[CH:39]=[CH:38][C:37]([S:42]([NH:14][CH2:13][CH2:1][CH2:2][C:3]([P:5](=[O:8])([O-:7])[O-:6])([P:9](=[O:11])([O-:12])[O-:10])[OH:4])(=[O:44])=[O:43])=[CH:36][CH:41]=1.[Na+:15].[Na+:15].[Na+:15].[Na+:15]

참가 물질

8

반응물 5

HCID 2088Alendronic Acid2회HCID 14798Sodium Hydroxide2회HCID 155402-Nitrobenzenesulfonyl chlorideHCID 5360545SodiumHCID 16760285Alendronate sodium anhydrous2회

생성물 1

HCID 86725127Sodium (4-(4-aminobenzenesulfonylamino)-1-hydroxybutane-1,1-diyl)bisphosphonate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium (4-(4-aminobenzenesulfonylamino)-1-hydroxybutane-1,1-diyl)bisphosphonate was synthesized using sodium alendronate. On this occasion, as the sodium alendronate, monosodium salt of (4-amino-1-hydroxybutane-1,1-diyl)bisphosphonic acid (manufactured by Zentiva) was used. An alendronate (34 g: 104 mmol) was added to 150 mL of pure water in a 500-mL beaker and was dissolved by adjusting the pH to 11 with an aqueous concentrated sodium hydroxide solution. To this solution was dropwise added nitrophenyl sulfonyl chloride (25 g: 110 mmol) dissolved in 100 mL of tetrahydrofuran. On this occasion, an aqueous sodium hydroxide solution was further added thereto to maintain the pH of the solution to 10 to 11. After completion of adding, this solution was stirred at room temperature for 2 hours. Subsequently, tetrahydrofuran was evaporated in vacuum, and the solution was adjusted to a pH of 4 to precipitate a solid, followed by cooling at 4 degrees Celsius overnight. Subsequently, the solid was collected by filtration and was washed with pure water and then dried to yield sodium (4-(4-aminobenzenesulfonylamino)-1-hydroxybutane-1,1-diyl)bisphosphonate.

후처리

  1. customSodium (4-(4-aminobenzenesulfonylamino)-1-hydroxybutane-1,1-diyl)bisphosphonate was synthesized
  2. dissolutionwas dissolved
  3. temperatureto maintain the pH of the solution to 10 to 11
  4. additionAfter completion of adding
  5. customSubsequently, tetrahydrofuran was evaporated in vacuum
  6. customto precipitate a solid
  7. temperatureby cooling at 4 degrees Celsius overnight
  8. filtrationSubsequently, the solid was collected by filtration
  9. washwas washed with pure water
  10. customdried

출처 및 근거

ORD 기록
ord-1159bc41e38a46ff925c9b59b7e0d7c9
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315683B2

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