HCID 14096709, compound → HCID 178501392, compound

HRID 845375Notes

Reaction equation

HRID 845375 reaction equation
[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:29]([NH:31][C@H:32]([C:43]([O:45][CH3:46])=[O:44])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:30])[CH2:11][C:12]1[N:16]=[CH:15][N:14](C2C=CC([N+]([O-])=O)=CC=2[N+]([O-])=O)[CH:13]=1)=[O:8]>CN(C=O)C.O.SC(O)C>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:29]([NH:31][C@H:32]([C:43]([O:45][CH3:46])=[O:44])[CH2:33][C:34]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[NH:36][CH:35]=1)=[O:30])[CH2:11][C:12]1[N:16]=[CH:15][NH:14][CH:13]=1)=[O:8]

Participants

5

Reactant 1

HCID 14096709HCID 14096709, compound

Product 1

HCID 178501392HCID 178501392, compoundYield 93.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 4713212Mercapto-ethanolSolvent

Procedure

To the solution containing 15.84 g (25 mmoles) of Glp-His(DNP)-Trp-OMe protected tripeptide in 100 ml of DMF and 40 ml of water, 4 ml of mercaptoethanol are added, then the pH-value of the solution is adjusted to 8 by adding TEA. The solution is left to stand at room temperature for 30 minutes, then evaporated to dryness under reduced pressure. The oily residue is thoroughly triturated with ether, filtered and dried. The thus-obtained product is dissolved in a little volume of methanol and crystallized by adding ether. The crystals are filtered and dried to give 10.92 g (93.5% yield) of the aimed compound, m.p.: 228°-232° C.

Workup

  1. additionare added
  2. additionby adding TEA
  3. waitThe solution is left
  4. customevaporated to dryness under reduced pressure
  5. customThe oily residue is thoroughly triturated with ether
  6. filtrationfiltered
  7. customdried
  8. dissolutionThe thus-obtained product is dissolved in a little volume of methanol
  9. customcrystallized
  10. additionby adding ether
  11. filtrationThe crystals are filtered
  12. customdried

Sources & evidence

ORD record
ord-9d2b161600a34deab23c0a18039a017c
Source dataset
uspto-grants-1988_07
Patent number
US04758552

Reaction notes

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