HCID 178418361, compound → HCID 178501443, compound

HRID 1982332Notes

Reaction equation

HRID 1982332 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:94][CH2:93][CH2:92][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]([N:59]([CH2:61][C:62]([NH:64][C@H:65]([C:72]([NH:74][C@H:75]([C:88]([O:90][CH3:91])=[O:89])[CH2:76][CH2:77][CH2:78][CH2:79][NH:80][C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])=[O:73])[CH2:66][C:67]1[N:71]=[CH:70][NH:69][CH:68]=1)=[O:63])[CH3:60])=[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].[H][H]>CO>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([N:23]1[CH2:94][CH2:93][CH2:92][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]([N:59]([CH2:61][C:62]([NH:64][C@H:65]([C:72]([NH:74][C@H:75]([C:88]([O:90][CH3:91])=[O:89])[CH2:76][CH2:77][CH2:78][CH2:79][NH:80][C:81]([O:83][C:84]([CH3:86])([CH3:87])[CH3:85])=[O:82])=[O:73])[CH2:66][C:67]1[N:71]=[CH:70][NH:69][CH:68]=1)=[O:63])[CH3:60])=[O:58])[OH:55])[CH2:50][CH:51]([CH3:52])[CH3:53])=[O:47])[CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1)=[O:37])[CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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

4

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178501442HCID 178501442, compound

Product 1

HCID 178501443HCID 178501443, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg of Z-Arg-Arg-Pro-Phe-His-Sta-Sar-His-Lys(Boc)-OMe (see Example 16) are dissolved in 2 ml of 95% strength MeOH and, after the addition of 10 mg of Pd-on-carbon (10% Pd), hydrogenated by passing hydrogen through until the starting material has disappeared completely (monitoring by thin layer ohromatography). The catalyst is filtered off, the filtrate is concentrated to dryness and the residue is dissolved in 2 ml of H2O and lyophilised, yielding H-Arg-Arg-Pro-Phe-His-Sta-Sar-His-Lys(Boc)-OMe; Rf (D)=0.15; Rf (M)=0.25; Rf (O)=0.22.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated to dryness
  3. dissolutionthe residue is dissolved in 2 ml of H2O

Sources & evidence

ORD record
ord-e02fb1be5e5b485c8fd1be6d6b297c00
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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