HCID 178455901, compound → HCID 178455900, compound

HRID 1982318Notes

Reaction equation

HRID 1982318 reaction equation
[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:97][CH2:96][CH2:95][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]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:75]([NH:77][C@H:78]([C:91]([O:93][CH3:94])=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][NH:83]C(OC(C)(C)C)=O)=[O:76])[CH2:69][C:70]1[N:74]=[CH:73][NH:72][CH:71]=1)=[O:66])[C@H:61]([CH2:63][CH3:64])[CH3:62])=[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]>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:97][CH2:96][CH2:95][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]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:75]([NH:77][C@H:78]([C:91]([O:93][CH3:94])=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][NH2:83])=[O:76])[CH2:69][C:70]1[N:74]=[CH:73][NH:72][CH:71]=1)=[O:66])[C@H:61]([CH2:63][CH3:64])[CH3:62])=[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

3

Reactant 1

HCID 178455901HCID 178455901, compound

Product 1

HCID 178455900HCID 178455900, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg of H-Arg-Arg-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe (Example 6) are dissolved in 1 ml of 95% strength TFA, left to stand for 25 minutes and then precipitation is effected by the addition of 10 ml of diisopropyl ether. The precipitate is filtered off, dried, dissolved in 4 ml of H2O and, in order to be converted into the acetate, the solution is slowly filtered through a column (φ=1 cm, length=12 cm) of weakly basic ion exchanger in acetate form. The eluate is concentrated to a small volume and lyophilised, yielding H-Arg-Arg-Pro-Phe-His-Sta-Ile-His-Lys-OMe; Rf (D)=0.15; Rf (M)=0.12; Rf (N)=0.09.

Workup

  1. waitleft
  2. customprecipitation
  3. additionis effected by the addition of 10 ml of diisopropyl ether
  4. filtrationThe precipitate is filtered off
  5. customdried
  6. dissolutiondissolved in 4 ml of H2O and, in order
  7. filtrationthe solution is slowly filtered through a column (φ=1 cm, length=12 cm) of weakly basic ion exchanger in acetate form
  8. concentrationThe eluate is concentrated to a small volume

Sources & evidence

ORD record
ord-f5580406c4134f9a9097864c348fc752
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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