HCID 178455946, compound → HCID 178455945, compound

HRID 65375Notes

Reaction equation

HRID 65375 reaction equation
[NH:1]([C:73]([O:75][CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)=[O:74])[C@H:2]([C:10]([NH:12][C@H:13]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:53]([NH:55][C@H:56]([C:69]([O:71][CH3:72])=[O:70])[CH2:57][CH2:58][CH2:59][CH2:60][NH:61]C(OC(C)(C)C)=O)=[O:54])[CH2:47][C:48]1[N:52]=[CH:51][NH:50][CH:49]=1)=[O:44])[C@H:39]([CH2:41][CH3:42])[CH3:40])=[O:36])[CH:32]([CH3:34])[CH3:33])=[O:29])[CH2:24][CH:25]([CH3:27])[CH3:26])=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>FC(F)(F)C(O)=O>[NH:1]([C:73]([O:75][CH2:76][C:77]1[CH:78]=[CH:79][CH:80]=[CH:81][CH:82]=1)=[O:74])[C@H:2]([C:10]([NH:12][C@H:13]([C:20]([NH:22][C@H:23]([C:28]([NH:30][C@H:31]([C:35]([NH:37][C@H:38]([C:43]([NH:45][C@H:46]([C:53]([NH:55][C@H:56]([C:69]([O:71][CH3:72])=[O:70])[CH2:57][CH2:58][CH2:59][CH2:60][NH2:61])=[O:54])[CH2:47][C:48]1[N:52]=[CH:51][NH:50][CH:49]=1)=[O:44])[C@H:39]([CH2:41][CH3:42])[CH3:40])=[O:36])[CH:32]([CH3:33])[CH3:34])=[O:29])[CH2:24][CH:25]([CH3:26])[CH3:27])=[O:21])[CH2:14][C:15]1[N:19]=[CH:18][NH:17][CH:16]=1)=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 178455946HCID 178455946, compound

Product 1

HCID 178455945HCID 178455945, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

80 mg of Z-Phe-His-Leu-Val-Ile-His-Lys(BOC)-OMe (Example 55) are dissolved in 800 μl of 95% trifluoroacetic acid (duration approximately 1 minute) and left to stand for 2 minutes. The product is then precipitated by the addition of 8 ml of diisopropyl ether, left to stand for 15 minutes at 0°, filtered off, and the precipitate is washed with diisopropyl ether and dried over KOH in a high vacuum. The powder is then dissolved in 1 ml of 90trifluoroethanol, precipitated by the addition of 10 ml of 3% MaHCO3 solution, filtered off, washed with H2O and dried over potassium hydroxide and phosphorus pentoxide in a high vacuum. To convert the resulting acid-free title compound into the acetate, the product is dissolved in 2 ml of 90% acetic acid and lyophilised. The title compound is a chromatographically homogeneous amorphous powder; Rf (B17)=0.08, Rf (B21)=0.65.

Workup

  1. waitleft
  2. customThe product is then precipitated by the addition of 8 ml of diisopropyl ether
  3. waitleft
  4. waitto stand for 15 minutes at 0°
  5. filtrationfiltered off
  6. washthe precipitate is washed with diisopropyl ether
  7. dry with materialdried over KOH in a high vacuum
  8. dissolutionThe powder is then dissolved in 1 ml of 90trifluoroethanol
  9. customprecipitated by the addition of 10 ml of 3% MaHCO3 solution
  10. filtrationfiltered off
  11. washwashed with H2O
  12. dry with materialdried over potassium hydroxide and phosphorus pentoxide in a high vacuum
  13. dissolutionthe product is dissolved in 2 ml of 90% acetic acid

Sources & evidence

ORD record
ord-d275df04b7b0493a8276f2cdbf7fd071
Source dataset
uspto-grants-1986_09
Patent number
US04613676

Reaction notes

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