Dimethylformamide → HCID 131712874, compound

HRID 2198664Notes

Reaction equation

HRID 2198664 reaction equation
[NH:1]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:54]([N:56]1[CH2:67][CH2:66][CH2:65][C@H:57]1[C:58]([O:60]C(C)(C)C)=[O:59])=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:39])[CH2:34][CH2:35][S:36][CH3:37])=[O:31])[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CN(C=O)C>C(O)(C(F)(F)F)=O>[NH:1]([C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])[C@H:2]([C:11]([NH:13][CH2:14][C:15]([NH:17][CH2:18][C:19]([NH:21][C@H:22]([C:30]([NH:32][C@H:33]([C:38]([NH:40][C@H:41]([C:54]([N:56]1[CH2:67][CH2:66][CH2:65][C@H:57]1[C:58]([OH:60])=[O:59])=[O:55])[CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])=[O:39])[CH2:34][CH2:35][S:36][CH3:37])=[O:31])[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:20])=[O:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 131712875HCID 131712875, compound

Product 1

HCID 131712874HCID 131712874, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 8 ml of TFA were dissolved 800 mg of Boc-Tyr-Gly-Gly-Phe-Met-Lys(Boc)-Pro-OBut, and the solution, after shaking at room temperature for 60 minutes, was concentrated. To the concentrate was added diethyl ether, followed by recovering the resulting precipitates by filtration and drying. The precipitates were dissolved in 10 ml of DMF, and 0.34 ml of TEA and 440 mg of Boc-ONB were added to the solution followed by stirring at 0° C. for 2 hours and at room temperature for 10 hours. The solution was evaporated under reduced pressure to dryness. To the residue was added diethyl ether. The resulting precipitates were recovered by filtration and then placed on a column (2.5×115 cm) of Sephadex LH-20. Elution was conducted with MeOH and fractions of 195 to 225 ml were collected, then the solvent was evaporated to dryness under reduced pressure. To the concentrate was added diethyl ether, and the mixture was subjected to filtration to give the product. Yield 680 mg (90.9%); m.p. 151° C. (decomp.); [α]D24 -28.0° (c=0.52, DMF); Rf1 =0.25, Rf2 =0.64.

Workup

  1. concentrationwas concentrated
  2. additionTo the concentrate was added diethyl ether
  3. customby recovering the resulting
  4. customprecipitates by filtration
  5. customdrying
  6. dissolutionThe precipitates were dissolved in 10 ml of DMF
  7. addition0.34 ml of TEA and 440 mg of Boc-ONB were added to the solution
  8. stirringby stirring at 0° C. for 2 hours and at room temperature for 10 hours
  9. customThe solution was evaporated under reduced pressure to dryness
  10. additionTo the residue was added diethyl ether
  11. customThe resulting precipitates
  12. filtrationwere recovered by filtration
  13. washElution
  14. customwere collected
  15. customthe solvent was evaporated to dryness under reduced pressure
  16. additionTo the concentrate was added diethyl ether
  17. filtrationthe mixture was subjected to filtration
  18. customto give the product

Sources & evidence

ORD record
ord-2d34c61c1076486b906278ba28671fa7
Source dataset
uspto-grants-1982_11
Patent number
US04358440

Reaction notes

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