HCID 12802416, compound → HCID 12802418, compound

HRID 1277386Notes

Reaction equation

HRID 1277386 reaction equation
[NH:1]([C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][NH:34]C(OC(C)(C)C)=O)=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1>FC(F)(F)C(O)=O>[NH:1]([C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])[C@H:2]([C:11]([NH:13][C@@H:14]([C:16]([NH:18][CH2:19][C:20]([NH:22][C@H:23]([C:31]([NH:33][NH2:34])=[O:32])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:21])=[O:17])[CH3:15])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 12802416HCID 12802416, compound

Product 1

HCID 12802418HCID 12802418, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

In 30 ml of trifluoroacetic acid is dissolved 3.5 g of Z-Tyr-(D)-Ala-Gly-Phe-NH-NH-BOC and the solution is allowed to stand at room temperature for 20 minutes. The trifluoroacetic acid is distilled offand the residue is treated with diethyl ether and collected by filtration. The resulting powders are dissolved in 10 ml of DMF and stirred with 1.4 ml of TEA. The DMF is distilled off and the residue is treated with water,collected by filtration and purified by reprecipitation with methanol-diethylether. 2.8 g (96%); m.p. 182°-184° C. (decomp.); [α]D22 -23.0° (c=0.5, DMF); Rf1 =0.17.

Workup

  1. distillationThe trifluoroacetic acid is distilled
  2. additionthe residue is treated with diethyl ether
  3. filtrationcollected by filtration
  4. dissolutionThe resulting powders are dissolved in 10 ml of DMF
  5. distillationThe DMF is distilled off
  6. additionthe residue is treated with water,collected by filtration
  7. custompurified by reprecipitation with methanol-diethylether

Sources & evidence

ORD record
ord-6e13d28bc21b4ff8a1fab476f3aa251b
Source dataset
uspto-grants-1981_07
Patent number
US04277394

Reaction notes

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