1-Amino-2-methylpropylphosphonic acid, (R)- → (R)-[1-(4'-Chlorobiphenyl-4-sulfonylamino)2-methylpropyl]-phosphonic Acid

HRID 2301265Notes

Reaction equation

HRID 2301265 reaction equation
[NH2:1][C@H:2]([P:6](=[O:9])([OH:8])[OH:7])[CH:3]([CH3:5])[CH3:4].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1>[OH-].[Na+].O1CCCC1>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([S:23]([NH:1][C@H:2]([P:6](=[O:8])([OH:7])[OH:9])[CH:3]([CH3:5])[CH3:4])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 27348871-Amino-2-methylpropylphosphonic acid, (R)-HCID 27947454'-Chlorobiphenyl-4-sulfonyl chloride

Product 1

HCID 9822461(R)-[1-(4'-Chlorobiphenyl-4-sulfonylamino)2-methylpropyl]-phosphonic Acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
22 °C

Procedure

250 mg (1.6 mmol) of (R)-(1-amino-2-methylpropyl)phosphonic acid were dissolved in 6 ml of a 1 M NaOH and 6 ml of tetrahydrofuran. 560 mg (1.96 mmol) of 4-chlorobiphenyl-4′-sulfonyl chloride were then added and the mixture was stirred at 22° C. overnight. The reaction mixture was concentrated, acidified with 2 M HCl and extracted with ethyl acetate. The 4-chlorobiphenyl4′-sulfonic acid resulting as a by-product precipitated and was separated off. After drying and concentrating the ethyl acetate phase, a solid was obtained.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionextracted with ethyl acetate
  3. customThe 4-chlorobiphenyl4′-sulfonic acid resulting as a by-product precipitated
  4. customwas separated off
  5. customAfter drying
  6. concentrationconcentrating the ethyl acetate phase
  7. customa solid was obtained

Sources & evidence

ORD record
ord-96ac817d95d9432eb8b1d9157ebe945e
Source dataset
uspto-grants-2002_12
Patent number
US06500811B2

Reaction notes

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