N-methyl-2-pyrrolidone → HCID 68840300, compound

HRID 1452438Notes

Reaction equation

HRID 1452438 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:14]([O:16][C:17](=[O:28])[C@H:18]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)[NH2:19])[CH3:15].CN1C(=O)CCC1.CCN=C=NCCCN(C)C.Cl>C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:14]([O:16][C:17](=[O:28])[C@H:18]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=1)[NH2:19])[CH3:15]

Participants

6

Reactant 4

HCID 13387N-methyl-2-pyrrolidone2×HCID 70364L-Tyrosine ethyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53401767HCID 53401767, compound

Product 1

HCID 68840300HCID 68840300, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL 3-necked round bottomed flask equipped with an overhead stirrer may be added 17.0 g of 3-(3-iodo-4-hydroxyphenyl)-2-propenoic acid, 12.25 g (0.0585 moles) or tyrosine ethyl ester, and 25 mL of NMP. The mixture may be stirred until a clear solution is obtained. The flask may be cooled in an ice-water bath, the 11.84 g (0.0619 moles) of EDCI HCl may be added in one portion, followed by 15 mL of NMP. The cooling bath may be removed after 2.5 hours, and the reaction may be allowed to continue overnight at room temperature. 71 mL of ethyl acetate may be added, and stirring may be maintained for 15 more minutes. The crude may then be transferred into a 500 mL separatory funnel, and extracted once with 75 mL of brine, then with two aliquots (75 and 35 mL) of 3% NaHCO3/14% NaCl, followed by 35 mL aliquots of 0.4M HCl/14% NaCl, and finally with brine. The organic phase may be dried over magnesium sulfate and treated with activated carbon, filtered and concentrated to a thick syrup, which may crystallize into a solid mass after a few hours. The product may be triturated in methylene chloride using mechanical stirring, then it may be recovered by filtration and dried under a nitrogen stream followed by high vacuum.

Workup

  1. customTo a 250 mL 3-necked round bottomed flask equipped with an overhead stirrer
  2. customis obtained
  3. temperatureThe flask may be cooled in an ice-water bath
  4. customThe cooling bath may be removed after 2.5 hours
  5. customthe reaction
  6. stirringstirring may
  7. temperaturebe maintained for 15 more minutes
  8. customThe crude may then be transferred into a 500 mL separatory funnel
  9. extractionextracted once with 75 mL of brine
  10. dry with materialThe organic phase may be dried over magnesium sulfate
  11. additiontreated with activated carbon
  12. filtrationfiltered
  13. concentrationconcentrated to a thick syrup, which
  14. custommay crystallize into a solid mass after a few hours
  15. customThe product may be triturated in methylene chloride using mechanical stirring
  16. filtrationit may be recovered by filtration
  17. customdried under a nitrogen stream

Sources & evidence

ORD record
ord-325a42402bb248258b47297fbd1c4a5a
Source dataset
uspto-grants-2009_01
Patent number
US07473417B2

Reaction notes

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