Water → HCID 11383300, compound

HRID 1160445Notes

Reaction equation

HRID 1160445 reaction equation
COC([C:5]1([C:20]([OH:22])=O)[CH:13]=[C:12]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[CH2:6]1)=O.[CH3:23][CH2:24][N:25]=C=NCCCN(C)C.Cl.[CH:35]1[CH:36]=[CH:37][C:38]2N(O)N=N[C:39]=2[CH:40]=1.O>C(OCC)(=O)C.C1(C)C=CC=CC=1.CN(C)C=O>[CH3:19][N:14]([S:15]([CH3:18])(=[O:16])=[O:17])[C:12]1[CH:11]=[C:7]([CH:6]=[C:5]([C:20]([NH:25][C@@H:24]([C:39]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:40]=2)[CH3:23])=[O:22])[CH:13]=1)[C:8]([OH:10])=[O:9]

Participants

7

Reactant 4

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68646137HCID 68646137, compound

Product 1

HCID 11383300HCID 11383300, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

A mixture of 3-(methoxycarbonyl)-5-[methyl(methylsulfonyl)amino]isophthalic acid obtained in Reference Example 6 11.5 g (40 mmol), WSC.HCl 8.43 g (44 mmol), HOBt.H2O 6.74 g (44 mmol), (R)-1-phenethylamine 5.6 mL (44 mmol) and N,N-dimethylformamide (100 mL) was stirred at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate/toluene=1:1 (300 mL) and washed with water (400 mL). The aqueous layer was extracted twice with ethyl acetate/toluene=1:1 (300 mL). The combined organic layer was dried on magnesium sulfate and the mixture was concentrated. The resulting solid was dissolved in 2N aqueous sodium hydroxide solution (80 mL), methanol (80 mL) and tetrahydrofuran (80 mL) and the mixture was stirred at room temperature for 15 hours. The solvent was concentrated and thereto was added water (100 mL) and the mixture was washed twice with ethyl acetate (100 mL). The aqueous layer was adjusted by adding 1N hydrochloric acid to pH=3 and the precipitated solid was collected by filtering and dried under vacuum to give 13.2 g (35.1 mmol) of the title compound. (yield: 88%).

Workup

  1. washwashed with water (400 mL)
  2. extractionThe aqueous layer was extracted twice with ethyl acetate/toluene=1:1 (300 mL)
  3. customThe combined organic layer was dried on magnesium sulfate
  4. concentrationthe mixture was concentrated
  5. dissolutionThe resulting solid was dissolved in 2N aqueous sodium hydroxide solution (80 mL)
  6. concentrationThe solvent was concentrated
  7. additionwas added water (100 mL)
  8. washthe mixture was washed twice with ethyl acetate (100 mL)
  9. additionby adding 1N hydrochloric acid to pH=3
  10. customthe precipitated solid was collected
  11. filtrationby filtering
  12. customdried under vacuum

Sources & evidence

ORD record
ord-5df52fc6f60d4b938299fb7d8e018f09
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

Loading…