Acetic Acid → phosphoric acid mono-(4-{4-[(2,6-dichloro-benzoylamino)-methyl]phenyl}-2-oxo-2H-pyridin-1-ylmethyl)ester

HRID 1042935Notes

Reaction equation

HRID 1042935 reaction equation
[Cl:1][C:2]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]([CH2:20][O:21][P:22](=[O:33])([O:28]C(C)(C)C)[O:23]C(C)(C)C)[C:16](=[O:34])[CH:15]=2)=[CH:10][CH:9]=1)=[O:5].C(O)(=O)C.O>C(#N)C>[Cl:39][C:35]1[CH:36]=[CH:37][CH:38]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][N:17]([CH2:20][O:21][P:22](=[O:23])([OH:33])[OH:28])[C:16](=[O:34])[CH:15]=2)=[CH:12][CH:13]=1)=[O:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 71149943phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester

Product 1

HCID 71149979phosphoric acid mono-(4-{4-[(2,6-dichloro-benzoylamino)-methyl]phenyl}-2-oxo-2H-pyridin-1-ylmethyl)esterYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester from the previous step was dissolved in 20 mL acetonitrile, 20 mL acetic acid and 20 mL water, and heated at 70° C. for four hours. All volatile components were evaporated under vacuum and the residue was dissolved in 10 mL DMF. Slow addition of acetonitrile (˜60 mL) precipitated the product which was filtered, washed with more acetonitrile and dried, giving phosphoric acid mono-(4-{4-[(2,6-dichloro-benzoylamino)-methyl]phenyl}-2-oxo-2H-pyridin-1-ylmethyl)ester (1.17 g, 56% over three steps) as a white powder.

Workup

  1. customAll volatile components were evaporated under vacuum
  2. dissolutionthe residue was dissolved in 10 mL DMF
  3. additionaddition of acetonitrile (˜60 mL)
  4. customprecipitated the product which
  5. filtrationwas filtered
  6. washwashed with more acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-37a17c812b6a482cbb2e337680250469
Source dataset
uspto-grants-2013_10
Patent number
US08558001B2

Reaction notes

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