HCID 178418361, compound → HCID 178455901, compound

HRID 1982317Notes

Reaction equation

HRID 1982317 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[CH2:97][CH2:96][CH2:95][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]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:75]([NH:77][C@H:78]([C:91]([O:93][CH3:94])=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][NH:83][C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])=[O:76])[CH2:69][C:70]1[N:74]=[CH:73][NH:72][CH:71]=1)=[O:66])[C@H:61]([CH2:63][CH3:64])[CH3:62])=[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[CH2:97][CH2:96][CH2:95][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]([NH:59][C@H:60]([C:65]([NH:67][C@H:68]([C:75]([NH:77][C@H:78]([C:91]([O:93][CH3:94])=[O:92])[CH2:79][CH2:80][CH2:81][CH2:82][NH:83][C:84]([O:86][C:87]([CH3:88])([CH3:89])[CH3:90])=[O:85])=[O:76])[CH2:69][C:70]1[N:74]=[CH:73][NH:72][CH:71]=1)=[O:66])[C@H:61]([CH2:63][CH3:64])[CH3:62])=[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 178455898HCID 178455898, compound

Product 1

HCID 178455901HCID 178455901, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

145 mg of Z-Arg-Arg-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe (Example 4) are dissolved in 2.5 ml of 95% strength MeOH and, after the addition of 15 mg of Pd-on-carbon, hydrogenated by passing hydrogen through and stirring with a small magnetic rod until the starting material has disappeared completely (according to thin layer chromatography monitoring). The whole is filtered, the filtrate is concentrated to dryness, dissolved in 3 ml of H2O and lyophilised, yielding H-Arg-Arg-Pro-Phe-His-Sta-Ile-His-Lys(Boc)-OMe; Rf (D)=0.32; Rf (M)=0.25; Rf (N)=0.3.

Workup

  1. filtrationThe whole is filtered
  2. concentrationthe filtrate is concentrated to dryness
  3. dissolutiondissolved in 3 ml of H2O

Sources & evidence

ORD record
ord-0c6e113fb664409d951d4150b5e60f58
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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