Dicyclohexylcarbodiimide → cyclo(-DTrp-DAsp-Thz-DVal-Leu-)

HRID 1196735Notes

Reaction equation

HRID 1196735 reaction equation
N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CC(C)C.N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@@H](C(O)=O)CC(=O)OC(C)(C)C.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:72][C@@H:73]([C:84]([NH:86][C@@H:87]([C:96]([N:98]1[CH2:120][S:119][CH2:118][C@H:99]1[C:100]([NH:102][C@@H:103]([C:107]([NH:109][C@H:110]([C:115]([OH:117])=[O:116])[CH2:111][CH:112]([CH3:114])[CH3:113])=[O:108])[CH:104]([CH3:106])[CH3:105])=[O:101])=[O:97])[CH2:88][C:89](=[O:95])[O:90]C(C)(C)C)=[O:85])[CH2:74][C:75]1[C:83]2[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=2)[NH:77][CH:76]=1>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH:98]1[CH2:120][S:119][CH2:118][C@H:99]1[C:100]([NH:102][C@@H:103]([C:107]([NH:109][C@H:110]([C:115]([OH:117])=[O:116])[CH2:111][CH:112]([CH3:113])[CH3:114])=[O:108])[CH:104]([CH3:105])[CH3:106])=[O:101].[NH:72]1[C:115](=[O:117])[C@H:110]([CH2:111][CH:112]([CH3:114])[CH3:113])[NH:109][C:107](=[O:108])[C@@H:103]([CH:104]([CH3:106])[CH3:105])[NH:102][C:100](=[O:101])[C@@H:99]2[CH2:118][S:119][CH2:120][N:98]2[C:96](=[O:97])[C@@H:87]([CH2:88][C:89](=[O:95])[OH:90])[NH:86][C:84](=[O:85])[C@H:73]1[CH2:74][C:75]1[C:83]2[C:78](=[CH:79][CH:80]=[CH:81][CH:82]=2)[NH:77][CH:76]=1

Participants

8

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1549133Fmoc-leucineHCID 70188164-tert-Butyl N-((9H-Fluoren-9-ylmethoxy)carbonyl)-D-aspartateHCID 131717388DTrp-DAsp(OtBu)-Thz-DVal-Leu

Product 2

HCID 10508218cyclo(-DTrp-DAsp-Thz-DVal-Leu-)HCID 131717387Thz-DVal-Leu

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Thz-DVal-Leu-resin which was prepared from Fmoc-Leu-resin in the same manner described in Example 4, was unpacked from a reaction column and allowed to react with 2.5 equivalents of the symmetrical acid anhydride of Fmoc-nAsp(OtBu)(prepared previously from Fmoc-DAsp(OtBu) and DCC) and DMAP(10 mg) in DMF at room temperature for 3 h with occasional shaking. After removal of excess reagents, the resin was washed successively with DMF, tert-amyl alcohol, acetic acid, tert-amyl alcohol and DMF, and repacked in a reaction column. The further solid-phase peptide synthesis was performed by the standard protocol described in Example 4. The resulting DTrp-DAsp(OtBu)-Thz-DVal-Leu-resin was treated in the same manner described in Example 4 to give the title compound.

Workup

  1. customwas unpacked from a reaction column
  2. customAfter removal of excess reagents
  3. washthe resin was washed successively with DMF, tert-amyl alcohol, acetic acid, tert-amyl alcohol and DMF
  4. customrepacked in a reaction column

Sources & evidence

ORD record
ord-8b1795a306fe47eb9e4ea9e027b575da
Source dataset
uspto-grants-1992_05
Patent number
US05114918

Reaction notes

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