Diethyl Ether → HCID 178512873, compound

HRID 1481662Notes

Reaction equation

HRID 1481662 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:37][CH2:36][CH2:35][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]1[CH2:34][CH2:33][CH2:32][C@H:17]1[C:18]([NH:20][CH2:21][C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])=[O:19])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:13])[NH2:12])=[O:4].CCOCC>Cl.O1CCOCC1>[NH:1]1[CH2:37][CH2:36][CH2:35][C@H:2]1[C:3]([NH:5][C@H:6]([C:14]([N:16]1[CH2:34][CH2:33][CH2:32][C@H:17]1[C:18]([NH:20][CH2:21][C:22]([N:24]1[CH2:31][CH2:30][CH2:29][C@H:25]1[C:26]([OH:28])=[O:27])=[O:23])=[O:19])=[O:15])[CH2:7][CH2:8][CH2:9][NH:10][C:11](=[NH:12])[NH2:13])=[O:4]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 178451948HCID 178451948, compound

Product 1

HCID 178512873HCID 178512873, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

3.02 g (5.8 mmol) of Boc-Pro-Arg-Pro-Gly-Pro were suspended in 10 ml of 2N hydrochloric acid in dioxane and were incubated at room temperature for 45 min. Then, dry ether was added, and the precipitate was washed by decantation with dry ether. It was reprecipitated with ether from absolute methanol. The resulting precipitate was dissolved in 7.5 ml of 30% ethanol and applied to Amberlyst A-21 (Aco−-form) column for acetate/hydrochloride salt exchange. Peptide was eluted with 200 ml of 30% ethanol, evaporated to dryness under vacuum and precipitated with absolute ether from methanol.

Workup

  1. washthe precipitate was washed by decantation with dry ether
  2. customIt was reprecipitated with ether from absolute methanol
  3. dissolutionThe resulting precipitate was dissolved in 7.5 ml of 30% ethanol
  4. washPeptide was eluted with 200 ml of 30% ethanol
  5. customevaporated to dryness under vacuum
  6. customprecipitated with absolute ether from methanol

Sources & evidence

ORD record
ord-7614bc71afdb4bf48a54b1ba89ce4823
Source dataset
uspto-grants-2016_08
Patent number
US09409947B2

Reaction notes

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