Ethanaminide → Trifluoroacetate

HRID 891475Notes

Reaction equation

HRID 891475 reaction equation
[N:1]1(C(OCC2C3C(=CC=CC=3)C3C2=CC=CC=3)=O)CC[CH2:6][C@H:2]1[C:3](O)=O.[CH2:26]([NH-:28])C.[NH:29]([C:59]([O:61]CC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:30]([C:56]([OH:58])=O)[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:55])[NH:36]S(C1C(C)=C(C)C2OC(C)(C)CCC=2C=1C)(=O)=O.[C:76]([OH:82])([C:78]([F:81])([F:80])[F:79])=[O:77].[C:83]1(OC)[CH:88]=[CH:87][CH:86]=CC=1.O>>[NH:28]([C:76]([CH3:78])=[O:77])[C@H:26]([C:59]([NH:29][C@H:30]([C:56]([NH:1][CH:2]([CH3:6])[CH3:3])=[O:58])[CH2:31][CH2:32][CH2:33][NH:34][C:35](=[NH:55])[NH2:36])=[O:61])[C@H:88]([CH2:87][CH3:86])[CH3:83].[F:79][C:78]([F:81])([F:80])[C:76]([O-:82])=[O:77]

Participants

6

Reactant 4

HCID 187872EthanaminideHCID 688135Fmoc-Pro-OHHCID 131725292TFA anisole waterHCID 178427573HCID 178427573, compound

Product 2

HCID 84468TrifluoroacetateHCID 178455893N-Ac-Ile-Arg-NHCH(CH3)2

Procedure

The procedure described in Example 1 can used but substituting Fmoc-Arg(Pbf)-[4-(4-N-isopropyl)methyl-3-methoxyphenoxy]butyryl AM resin for Fmoc-Pro Sieber ethylamide resin and omitting the coupling with Fmoc-Arg(Pmc). Upon completion of the synthesis the peptide can be cleaved from the resin using a mixture of (95:2.5:2.5) TFA/anisole/water for 3 hr. The peptide solution can be concentrated in vacuo and then precipitated with diethyl ether. The crude peptide can be purified by HPLC using C-18 column and with a solvent mixture varying over 50 minutes in a gradient from 5% to 100% acetonitrile-water containing 0.01% TFA. The pure fractions can be lyophilized to give N-Ac-Ile-Arg-NHCH(CH3)2 as trifluoroacetate salt.

Workup

  1. concentrationThe peptide solution can be concentrated in vacuo
  2. customprecipitated with diethyl ether
  3. customThe crude peptide can be purified by HPLC

Sources & evidence

ORD record
ord-8166142184894084b45df7c2c480d4a0
Source dataset
uspto-grants-2006_02
Patent number
US07001984B2

Reaction notes

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