HCID 178453388, compound → HCID 178453389, compound

HRID 1482157Notes

Reaction equation

HRID 1482157 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:13]([NH:15][C@H:16]([C:27]([N:29]1[CH2:88][CH2:87][CH2:86][C@H:30]1[C:31]([NH:33][C@H:34]([C:45]([NH:47][C@H:48]([C:56]([NH:58][C@H:59]([C:67]([NH:69][C@H:70]([C:83]([NH2:85])=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][NH:75][C:76]([O:78][C:79]([CH3:82])([CH3:81])[CH3:80])=[O:77])=[O:68])[CH2:60][CH2:61][CH2:62][NH:63][C:64](=[NH:66])[NH2:65])=[O:57])[CH2:49][CH2:50][CH2:51][NH:52][C:53](=[NH:55])[NH2:54])=[O:46])[CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)=[O:32])=[O:28])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)=[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:27]([N:29]1[CH2:88][CH2:87][CH2:86][C@H:30]1[C:31]([NH:33][C@H:34]([C:45]([NH:47][C@H:48]([C:56]([NH:58][C@H:59]([C:67]([NH:69][C@H:70]([C:83]([NH2:85])=[O:84])[CH2:71][CH2:72][CH2:73][CH2:74][NH:75][C:76]([O:78][C:79]([CH3:82])([CH3:80])[CH3:81])=[O:77])=[O:68])[CH2:60][CH2:61][CH2:62][NH:63][C:64](=[NH:65])[NH2:66])=[O:57])[CH2:49][CH2:50][CH2:51][NH:52][C:53](=[NH:54])[NH2:55])=[O:46])[CH2:35][C:36]1[C:44]2[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH:38][CH:37]=1)=[O:32])=[O:28])[CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1)=[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 178453388HCID 178453388, compound

Product 1

HCID 178453389HCID 178453389, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A methanol solution of 1.00 equivalent of 2TPB.Z-TrpTrp-Pro-Trp-Arg-Arg-Lys(Boc)-NH2 (Mw=1347.5; purity=64.0%) was passed several times through a column containing a methanol washed resin IRA 958 (or Amberjet Cl 1000; 6.00 equivalents). After checking the exchange by HPLC, the resin was filtered, washed three times. The combined organic phases were partially concentrated in vacuo and then diluted with water. Finally, 2% (weight) of Pd catalyst were added and the suspension hydrogenated for at least 3 hours at 40° C. The catalyst was filtered off, washed three times with a mixture of methanol/water. The combined filtrates were evaporated in vacuo, the residue suspended in DMA and further concentrated in order to eliminate the remaining water. After checking the water content, the solution was titrated by HCl (0.1 N), AgNO3 (0.1 N) or NMR and further used without any purification.

Workup

  1. filtrationthe resin was filtered
  2. washwashed three times
  3. concentrationThe combined organic phases were partially concentrated in vacuo
  4. additiondiluted with water
  5. additionFinally, 2% (weight) of Pd catalyst were added
  6. waitthe suspension hydrogenated for at least 3 hours at 40° C
  7. filtrationThe catalyst was filtered off
  8. washwashed three times
  9. additionwith a mixture of methanol/water
  10. customThe combined filtrates were evaporated in vacuo
  11. concentrationfurther concentrated in order
  12. customfurther used without any purification

Sources & evidence

ORD record
ord-3babebd7d1594df39cb62877e82aaa11
Source dataset
uspto-grants-2016_08
Patent number
US09409946B2

Reaction notes

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