Ammonia → HCID 178445979, compound

HRID 1982334Notes

Reaction equation

HRID 1982334 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:87][CH2:86][CH2:85][C@H:24]1[C:25]([NH:27][C@H:28]([C:36]([NH:38][C@H:39]([C:46]([NH:48][C@H:49]([C@H:54]([CH2:56][C:57]([N:59]([CH2:61][C:62]([NH:64][C@H:65]([C:72]([NH:74][C@H:75]([C:81]([O:83]C)=[O:82])[CH2:76][CH2:77][CH2:78][CH2:79][NH2:80])=[O:73])[CH2:66][C:67]1[N:71]=[CH:70][NH:69][CH:68]=1)=[O:63])[CH3:60])=[O:58])[OH:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:20])[NH2:19])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].FC(F)(F)C([O-])=O.N>O>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:87][CH2:86][CH2:85][C@H:24]1[C:25]([NH:27][C@H:28]([C:36]([NH:38][C@H:39]([C:46]([NH:48][C@H:49]([C@H:54]([CH2:56][C:57]([N:59]([CH2:61][C:62]([NH:64][C@H:65]([C:72]([NH:74][C@H:75]([C:81]([OH:83])=[O:82])[CH2:76][CH2:77][CH2:78][CH2:79][NH2:80])=[O:73])[CH2:66][C:67]1[N:71]=[CH:70][NH:69][CH:68]=1)=[O:63])[CH3:60])=[O:58])[OH:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])=[O:22])[CH2:14][CH2:15][CH2:16][NH:17][C:18](=[NH:19])[NH2:20])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 84468TrifluoroacetateHCID 178501450HCID 178501450, compound

Product 1

HCID 178445979HCID 178445979, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

110 mg of H-Arg-Arg-Pro-Phe-His-Sta-Sar-His-Lys-OMe (in the form of the trifluoroacetate; see Example 18) are dissolved in 1 ml of H2O and the pH value is adjusted to 5.0 with 0.5N NH3. After the addition of 20 μl of a 1% aqueous trypsin solution, the pH value is maintained at 5.0 by means of a pH stat while stirring at room temperature and adding 0.1N NH3. After approximately 10-15 minutes the absorption of the base is complete. The solution is acidified with 200 μl of glacial acetic acid, heated for 2 minutes in a boiling water bath, and lyophilised. In order to be converted into the acetate, the residue is dissolved in H2O and filtered slowly through a column (φ=0.7 cm; length=8 cm) of weakly basic ion exchanger (formexample Merck No. II) equilibrated in 0.05N acetic acid. The eluate is concentrated to a small volume and lyophilised, yielding H-Arg-Arg-Pro-Phe-His-Sta-Sar-His-Lys-OH (in acetate form) as an amorphous, readily water-soluble powder; Rf (D)=0.03; Rf (M)=0.03; Rf (O)=0.03.

Workup

  1. additionAfter the addition of 20 μl of a 1% aqueous trypsin solution
  2. temperaturethe pH value is maintained at 5.0 by means of a pH stat
  3. customAfter approximately 10-15 minutes the absorption of the base
  4. temperatureheated for 2 minutes in a boiling water bath
  5. dissolutionthe residue is dissolved in H2O
  6. filtrationfiltered slowly through a column (φ=0.7 cm; length=8 cm) of weakly basic ion exchanger (formexample Merck No. II)
  7. concentrationThe eluate is concentrated to a small volume

Sources & evidence

ORD record
ord-39fa849ff232496d9c1ce2f753ee6ed7
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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