Glycine → HCID 178512888, compound

HRID 616486Notes

Reaction equation

HRID 616486 reaction equation
F.[NH:2](C(OCC1C=CC=CC=1)=O)[C@H:3]([C:11]([NH:13][C@H:14]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:40]([NH:42][C@H:43]([C:51]([NH2:53])=[O:52])[CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:41])[CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:30])=[O:26])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:24])[NH:20][N+]([O-])=O)=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.N[C@H](C(O)=O)CCCNC(=N)N.NCC(O)=O.N[C@H](C(O)=O)CC1C=CC=CC=1>>[NH2:2][C@H:3]([C:11]([NH:13][C@H:14]([C:25]([NH:27][CH2:28][C:29]([NH:31][C@H:32]([C:40]([NH:42][C@H:43]([C:51]([NH2:53])=[O:52])[CH2:44][C:45]1[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=1)=[O:41])[CH2:33][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)=[O:30])=[O:26])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:20])[NH2:24])=[O:12])[CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 5

HCID 750GlycineHCID 6140L-PhenylalanineHCID 14917Hydrofluoric AcidHCID 178418600HCID 178418600, compoundHCID 178512176HCID 178512176, compound

Product 1

HCID 178512888HCID 178512888, compound

Procedure

In 6-ml. of anhydrous hydrogen fluoride was dissolved 500 mg. of Z-Phe-Arg(NO2)-Gly-Phe-Phe-NH2 and the solution was stirred at -10° C for 40 minutes. The hydrogen fluoride was distilled off and the residue was dissolved in 10 ml. of water. The solution was passed through a column (0.9 × 15 cm) of Amberlite IRA-410(acetate-form) which was washed with water. The effluent was combined with the washings and the combined solution was lyophilized. The procedure yielded 402 mg. of the above-indicated compound. Amino acid analysis: Arg, 1.01; Gly, 0.98; Phe, 2.94 (peptide content 86.2%).

Workup

  1. distillationThe hydrogen fluoride was distilled off
  2. dissolutionthe residue was dissolved in 10 ml
  3. washwas washed with water
  4. customThe procedure yielded 402 mg

Sources & evidence

ORD record
ord-027c3a43ae8744db87fcfed1d34e55bf
Source dataset
uspto-grants-1978_02
Patent number
US04073890

Reaction notes

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