Hydrochloric Acid → HCID 178455904, compound

HRID 1448269Notes

Reaction equation

HRID 1448269 reaction equation
[C:1]([O:8][NH:9][CH2:10][C:11]([NH:13][C@H:14]([C:32]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:51]([NH:53][C@H:54]([C:59]([NH:61][C@H:62]([C:69]([N:71]1[CH2:86][CH2:85][CH2:84][C@H:72]1[C:73]([NH:75][C@H:76]([C:81]([OH:83])=[O:82])[C@H:77]([CH2:79][CH3:80])[CH3:78])=[O:74])=[O:70])[CH2:63][C:64]1[N:68]=[CH:67][NH:66][CH:65]=1)=[O:60])[C@H:55]([CH2:57][CH3:58])[CH3:56])=[O:52])[CH2:43][C:44]1[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=1)=[O:40])[CH:36]([CH3:38])[CH3:37])=[O:33])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:31])[NH:20][S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:12])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Cl.O1CCOC[CH2:89]1>>[C:1]([O:8][NH:9][C@H:10]([C:11]([NH:13][C@H:14]([C:32]([NH:34][C@H:35]([C:39]([NH:41][C@H:42]([C:51]([NH:53][C@H:54]([C:59]([NH:61][C@H:62]([C:69]([N:71]1[CH2:86][CH2:85][CH2:84][C@H:72]1[C:73]([NH:75][C@H:76]([C:81]([OH:83])=[O:82])[C@H:77]([CH2:79][CH3:80])[CH3:78])=[O:74])=[O:70])[CH2:63][C:64]1[N:68]=[CH:67][NH:66][CH:65]=1)=[O:60])[C@H:55]([CH2:57][CH3:58])[CH3:56])=[O:52])[CH2:43][C:44]1[CH:45]=[CH:46][C:47]([OH:50])=[CH:48][CH:49]=1)=[O:40])[CH:36]([CH3:38])[CH3:37])=[O:33])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:31])[NH:20][S:21]([C:24]1[CH:30]=[CH:29][C:27]([CH3:28])=[CH:26][CH:25]=1)(=[O:23])=[O:22])=[O:12])[CH3:89])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178455905HCID 178455905, compound

Product 1

HCID 178455904HCID 178455904, compoundYield 84%

Procedure

0.6 g. (0.5 mmoles) of Boc-Arg(Tos)-Val-Tyr-Ile-His-Pro-Ile-OH (prepared in Step 2 of Example 1) are dissolved in 5 ml. of a 8 M solution of hydrochloric acid in dioxane. The solution is allowed to stand for 20 minutes whereupon the free heptapeptide (Rf4 = 0.1) is precipitated with dry ether, filtered and washed with ether. It is immediately dissolved in 20 ml. of dimethyl formamide, the pH-value is adjusted to 8 with triethyl amine and 0.7 g. (1.9 mmoles) of Boc-OAla-OPFP are added. After 30 minutes the solution is evaporated and the residue is dissolved in 30 ml. of a 3:1 mixture of chloroform and dimethyl formamide. The solution is shaken with a 10% aqueous citric acid solution and subsequently with water. After drying and evaporation the residue is triturated with ethyl acetate, filtered and washed to give 0.55 g. (84%) of the title compound. Rf4 = 0.43; Rf5 = 0.80.

Workup

  1. customis precipitated with dry ether
  2. filtrationfiltered
  3. washwashed with ether
  4. dissolutionIt is immediately dissolved in 20 ml
  5. customAfter 30 minutes the solution is evaporated
  6. dissolutionthe residue is dissolved in 30 ml
  7. additionof a 3:1 mixture of chloroform and dimethyl formamide
  8. customAfter drying
  9. customevaporation the residue
  10. customis triturated with ethyl acetate
  11. filtrationfiltered
  12. washwashed
  13. customto give 0.55 g

Sources & evidence

ORD record
ord-11479c0e20734745a6f0929f7274880f
Source dataset
uspto-grants-1979_12
Patent number
US04179433

Reaction notes

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