Ammonia → HCID 178455894, compound

HRID 1982306Notes

Reaction equation

HRID 1982306 reaction equation
[NH:1]1[CH2:85][CH2:84][CH2:83][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:82][CH2:81][CH2:80][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:40][C@H:41]([C@H:46]([CH2:48][C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:67]([NH:69][C@H:70]([C:76]([O:78]C)=[O:77])[CH2:71][CH2:72][CH2:73][CH2:74][NH2:75])=[O:68])[CH2:61][C:62]1[N:66]=[CH:65][NH:64][CH:63]=1)=[O:58])[C@H:53]([CH2:55][CH3:56])[CH3:54])=[O:50])[OH:47])[CH2:42][CH:43]([CH3:45])[CH3:44])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4].C(O)(C(F)(F)F)=O.N>O>[NH:1]1[CH2:85][CH2:84][CH2:83][C@H:2]1[C:3]([NH:5][C@H:6]([C:13]([N:15]1[CH2:82][CH2:81][CH2:80][C@H:16]1[C:17]([NH:19][C@H:20]([C:28]([NH:30][C@H:31]([C:38]([NH:40][C@H:41]([C@H:46]([CH2:48][C:49]([NH:51][C@H:52]([C:57]([NH:59][C@H:60]([C:67]([NH:69][C@H:70]([C:76]([OH:78])=[O:77])[CH2:71][CH2:72][CH2:73][CH2:74][NH2:75])=[O:68])[CH2:61][C:62]1[N:66]=[CH:65][NH:64][CH:63]=1)=[O:58])[C@H:53]([CH2:55][CH3:56])[CH3:54])=[O:50])[OH:47])[CH2:42][CH:43]([CH3:44])[CH3:45])=[O:39])[CH2:32][C:33]1[N:37]=[CH:36][NH:35][CH:34]=1)=[O:29])[CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:18])=[O:14])[CH2:7][C:8]1[N:12]=[CH:11][NH:10][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 6422Trifluoroacetic acidHCID 178455895HCID 178455895, compound

Product 1

HCID 178455894HCID 178455894, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

370 mg of H-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys-OMe×5 TFA are dissolved in 8 ml of H2O. The pH value is increased to 5.0 with 0.3N NH3, whereupon 40 μl of a 1% aqueous solution of trypsin are added and the pH value is maintained constant by means of a pH stat with the addition of 0.3N NH3. The absorption of base is complete after approximately 40 minutes. 1 ml of glacial acetic acid is added, the whole is heated for 2 minutes in a boiling water bath, concentrated to approximately 3 ml and lyophilised. The residue is dissolved in 3 ml of 0.05N AcOH, converted into the acetate by slowly being filtered through a column (φ=1 cm, length=10 cm) of weakly basic ion exchanger (Merck No. II) in acetate form, and the eluate is again lyophilised, yielding H-Pro-His-Pro-Phe-His-Sta-Ile-His-Lys-OH×AcOH in the form of amorphous white powder; Rf (D)=0.12; Rf (K)=0.14.

Workup

  1. additionare added
  2. customThe absorption of base
  3. addition1 ml of glacial acetic acid is added
  4. temperaturethe whole is heated for 2 minutes in a boiling water bath
  5. concentrationconcentrated to approximately 3 ml
  6. dissolutionThe residue is dissolved in 3 ml of 0.05N AcOH
  7. filtrationby slowly being filtered through a column (φ=1 cm, length=10 cm) of weakly basic ion exchanger (Merck No. II) in acetate form

Sources & evidence

ORD record
ord-3ce72958219e467fb061df3308b4e814
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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