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Triethylamine → HCID 89614637, compound

HRID 578612
Notes
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Reaction equation

HRID 578612 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:8][P:9]([CH2:14][CH:15]([CH2:25][OH:26])[CH2:16][P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])(=[O:13])[O:10][CH2:11][CH3:12])[CH3:7].C(N(CC)CC)C>ClCCl>[CH2:19]([O:18][P:17]([CH2:16][CH:15]([CH2:25][O:26][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:14][P:9](=[O:13])([O:10][CH2:11][CH3:12])[O:8][CH2:6][CH3:7])(=[O:24])[O:21][CH2:22][CH3:23])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11759759HCID 11759759, compound

Product 1

HCID 89614637HCID 89614637, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonylchloride (2.2 ml, 28.6 mmol) was added dropwise at 0° C. to a solution of 2-hydroxymethyl-1,3-propylene-bisphosphonic acid tetraethylester (9.0 g, 26.0 mmol) and triethylamine (4.0 ml, 28.6 mmol, 1.1 eq.) in anhydrous dichloromethane (90 ml). The reaction mixture was stirred for 30 min at 0° C. and for 2 h at room temperature. After concentrating in vacuo deionized water (100 ml) was added and the mixture was extracted with ethylacetate (3×100 ml). The combined organic phases were dried with anhydrous sodium sulphate. After removal of the solvent under reduced pressure the obtained crude product was purified by column chromatography (eluent: ethylacetate/methanol 9:1). 9.37 g (85% yield) of the product was obtained as a colorless oil.

Workup

  1. concentrationAfter concentrating in vacuo deionized water (100 ml)
  2. additionwas added
  3. extractionthe mixture was extracted with ethylacetate (3×100 ml)
  4. dry with materialThe combined organic phases were dried with anhydrous sodium sulphate
  5. customAfter removal of the solvent under reduced pressure the
  6. customobtained crude product
  7. customwas purified by column chromatography (eluent: ethylacetate/methanol 9:1)

Sources & evidence

ORD record
ord-6e35ca9df40c446ea78730aba48a175c
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09040602B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes