HCID 178453390, compound → HCID 178453391, compound

HRID 1482155Notes

Reaction equation

HRID 1482155 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:51]([NH2:53])=[O:52])[CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:36])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:34])[NH2:33])=[O:25])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:23])[NH2:22])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>CO>[NH2:1][C@H:2]([C:13]([NH:15][C@H:16]([C:24]([NH:26][C@H:27]([C:35]([NH:37][C@H:38]([C:51]([NH2:53])=[O:52])[CH2:39][CH2:40][CH2:41][CH2:42][NH:43][C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])=[O:36])[CH2:28][CH2:29][CH2:30][NH:31][C:32](=[NH:33])[NH2:34])=[O:25])[CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:22])[NH2:23])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1

Participants

3

Reactant 1

HCID 178453390HCID 178453390, compound

Product 1

HCID 178453391HCID 178453391, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The methanol solution of 1.00 equivalent of 2TPB.Z-Trp-Arg-Arg-Lys(Boc)-NH2 (Mw=878.11) were passed several times through a column containing 6.00 equivalents of a methanol washed resin IRA 958 (Mw=1000). After checking the exchange by HPLC, the resin was filtered and washed three times with methanol. The combined organic phases were partially concentrated in vacuo. The concentrated solution was diluted with water and Pd catalyst were added. The suspension was then hydrogenated for at least 3 hours at 35±5° C. The catalyst was filtered off and washed twice with methanol. The filtrate was evaporated in vacuo, the residue dissolved in DMA and further concentrated in order to eliminate the remaining water. After the water content was checked, the precipitate was dissolved in DMA and partially evaporated in vacuo in order to adapt the weight of the solution. The final solution was titrated by 0.1N HCl and further used without any purification.

Workup

  1. filtrationthe resin was filtered
  2. washwashed three times with methanol
  3. concentrationThe combined organic phases were partially concentrated in vacuo
  4. additionThe concentrated solution was diluted with water and Pd catalyst
  5. additionwere added
  6. waithydrogenated for at least 3 hours at 35±5° C
  7. filtrationThe catalyst was filtered off
  8. washwashed twice with methanol
  9. customThe filtrate was evaporated in vacuo
  10. dissolutionthe residue dissolved in DMA
  11. concentrationfurther concentrated in order
  12. dissolutionthe precipitate was dissolved in DMA
  13. custompartially evaporated in vacuo in order
  14. customfurther used without any purification

Sources & evidence

ORD record
ord-4e4cad12ca904b50b39dce1929095e17
Source dataset
uspto-grants-2016_08
Patent number
US09409946B2

Reaction notes

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