HCID 67852048, compound → HCID 131710328, compound

HRID 1658297Notes

Reaction equation

HRID 1658297 reaction equation
C(OCC)(=O)C.N1C=CC=CC=1CC(O)=O.O.[CH2:18]1[CH:23]([C:24]([NH:26][CH:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]2[NH:33][CH:32]=[N:31][CH:30]=2)=[O:25])[NH:22][C:20](=[O:21])[CH2:19]1.[CH:37]1[CH:42]=[C:41]2[C:43]([CH2:46][CH:47]([NH2:57])[C:48]([NH:50][CH:51]([C:54]([OH:56])=O)[CH2:52][OH:53])=[O:49])=[CH:44][NH:45][C:40]2=[CH:39][CH:38]=1.[CH3:58][O:59][C:60]([C@@H:62]([NH2:71])[CH2:63][C:64]1[CH:69]=[CH:68][C:67]([OH:70])=[CH:66][CH:65]=1)=[O:61]>>[CH2:18]1[CH:23]([C:24]([NH:26][CH:27]([C:34]([OH:36])=[O:35])[CH2:28][C:29]2[NH:33][CH:32]=[N:31][CH:30]=2)=[O:25])[NH:22][C:20](=[O:21])[CH2:19]1.[NH2:57][C@H:47]([C:48]([NH:50][C@H:51]([C:54]([NH:71][C@H:62]([C:60]([O:59][CH3:58])=[O:61])[CH2:63][C:64]1[CH:65]=[CH:66][C:67]([OH:70])=[CH:68][CH:69]=1)=[O:56])[CH2:52][OH:53])=[O:49])[CH2:46][C:43]1[C:41]2[C:40](=[CH:39][CH:38]=[CH:37][CH:42]=2)[NH:45][CH:44]=1

Participants

3

Reactant 2

HCID 67852048HCID 67852048, compoundHCID 131710329HCID 131710329, compound

Product 1

HCID 131710328HCID 131710328, compound

Procedure

The reaction solution containing pyroglu-his azide, prepared as described in Example 22, is cooled to a temperature of -40°C., and to this is added a solution of 1.1 g. of trp-ser-tyr-OMe trifluoroacetate, as prepared in Example 4, 5, 6 and 7, in 4 ml. of degassed dimethylformamide. The pH of the resulting solution is adjusted to 8.0 by the addition of diisopropylethylamine, and the mixture is maintained at a temperature of -5°C. (with periodic adjustment of the pH to 8.0 by addition of diisopropylethylamine) for a period of 18 hours, at the end of which time the reaction to form the pentapeptide is substantially complete as shown by thin layer chromatography on silica gel G using the solvent system ethyl acetate-pyridine-acetic acid-water (10:5:1:3). The reaction solution is evaporated in vacuo; the residual material is dissolved in 50 ml. butanol; the butanol solution is washed with three 25 ml.-portions of water; the combined water washings are extracted with six 10 ml.-portions of butanol; and the combined butanol solutions are evaporated to a small volume. The crystalline material which precipitates is recovered by filtration, dried and further purified by chromatography on a silica gel column to give 0.5 g. of substantially pure pyroglu-his-trp-ser-tyr-OMe.

Workup

  1. customThe reaction solution is evaporated in vacuo
  2. dissolutionthe residual material is dissolved in 50 ml
  3. washthe butanol solution is washed with three 25 ml
  4. extractionthe combined water washings are extracted with six 10 ml
  5. customand the combined butanol solutions are evaporated to a small volume
  6. customThe crystalline material which precipitates
  7. filtrationis recovered by filtration
  8. customdried
  9. customfurther purified by chromatography on a silica gel column
  10. customto give 0.5 g

Sources & evidence

ORD record
ord-5454107c949048458cd162f8eac0599b
Source dataset
uspto-grants-1976_06
Patent number
US03963691

Reaction notes

Loading…