Diethyl Ether → HCID 178512900, compound

HRID 1481660Notes

Reaction equation

HRID 1481660 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([N:12]1[CH2:30][CH2:29][CH2:28][C@H:13]1[C:14]([NH:16][CH2:17][C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])=[O:15])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].CCOCC>Cl.O1CCOCC1>[NH2:1][C@H:2]([C:10]([N:12]1[CH2:30][CH2:29][CH2:28][C@H:13]1[C:14]([NH:16][CH2:17][C:18]([N:20]1[CH2:27][CH2:26][CH2:25][C@H:21]1[C:22]([OH:24])=[O:23])=[O:19])=[O:15])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 178454179Boc-Arg-Pro-Gly-Pro

Product 1

HCID 178512900HCID 178512900, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

4.23 g (5.8 mmol) of Boc-Arg-Pro-Gly-Pro-OH were suspended in 10 ml of 2N hydrochloric acid in dioxane and 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-e1c5c8acb7a145249e673c878c0520c0
Source dataset
uspto-grants-2016_08
Patent number
US09409947B2

Reaction notes

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