Trifluoroacetic acid → Z-Tyr-(D)-Gln-Gly-MePhe-NHNHCSNH2

HRID 1156950Notes

Reaction equation

HRID 1156950 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@@H:2]([C:8]([NH:10][CH2:11][C:12]([N:14]([CH3:30])[C@H:15]([C:23]([NH:25][NH:26][C:27]([NH2:29])=[S:28])=[O:24])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6].FC(F)(F)C(O)=O.[NH:45]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[C@H:46]([C:55](O)=[O:56])[CH2:47][C:48]1[CH:53]=[CH:52][C:51]([OH:54])=[CH:50][CH:49]=1>CN(C=O)C>[NH:45]([C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59])[C@H:46]([C:55]([NH:1][C@@H:2]([C:8]([NH:10][CH2:11][C:12]([N:14]([CH3:30])[C@H:15]([C:23]([NH:25][NH:26][C:27]([NH2:29])=[S:28])=[O:24])[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:13])=[O:9])[CH2:3][CH2:4][C:5](=[O:7])[NH2:6])=[O:56])[CH2:47][C:48]1[CH:49]=[CH:50][C:51]([OH:54])=[CH:52][CH:53]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 712438N-benzyloxycarbonyl-l-tyrosineHCID 12802637HCID 12802637, compound

Product 1

HCID 12802639Z-Tyr-(D)-Gln-Gly-MePhe-NHNHCSNH2

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.60 g of BOC-(D)-Gln-Gly-MePhe-NHNHCSNH2 is treated with trifluoroacetic acid and dissolved in 10 ml of DMF. The solution is neutralized with 0.19 ml of TEA, and 0.54 g of Z-Tyr ONB is added. The mixture is stirred for 15 hours. The DMF is distilled off and the residue is treated with ethyl acetate and filtered to obtain a powder, which is further reprecipitated from methanol-ether. Yield 0.54 g; m.p. 128°-133° C.; [α]D24 -72.4° (c=1.1, DMF); Rf1 0.13.

Workup

  1. additionis added
  2. distillationThe DMF is distilled off
  3. additionthe residue is treated with ethyl acetate
  4. filtrationfiltered
  5. customto obtain a powder, which
  6. customis further reprecipitated from methanol-ether

Sources & evidence

ORD record
ord-773ce6836a374110bed39600aa4006b1
Source dataset
uspto-grants-1982_06
Patent number
US04337247

Reaction notes

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