HCID 131713875, compound → HCID 178446006, compound

HRID 1632421Notes

Reaction equation

HRID 1632421 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:5]([NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:19]([NH:21][C@H:22]([C:26]([NH:28][C@H:29]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:51]([NH:53][C@H:54]([C:60]([NH:62][C@H:63]([C:66]([NH:68][C@H:69]([C:74]([NH:76][C@H:77]([C:85]([NH:87][C@H:88]([C:91]([NH:93][C@H:94]([C:110]([NH:112][C@H:113]([C:119]([OH:121])=[O:120])[CH2:114][CH2:115][C:116](=[O:118])[OH:117])=[O:111])[CH2:95][CH2:96][CH2:97][CH2:98][NH:99]S(C1C=CC(C)=CC=1)(=O)=O)=[O:92])[CH2:89][OH:90])=[O:86])[CH2:78][CH2:79][CH2:80][NH:81][C:82](=[NH:84])[NH2:83])=[O:75])[CH2:70][CH:71]([CH3:73])[CH3:72])=[O:67])[CH2:64][OH:65])=[O:61])[CH2:55][CH2:56][C:57](=[O:59])[OH:58])=[O:52])[CH2:46][CH2:47][C:48](=[O:50])[NH2:49])=[O:43])[CH2:38][CH:39]([CH3:41])[CH3:40])=[O:35])[CH2:30][C:31](=[O:33])[NH2:32])=[O:27])[C@@H:23]([CH3:25])[OH:24])=[O:20])[CH2:17][OH:18])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH2:3][OH:4]>N>[NH2:1][C@H:2]([C:5]([NH:7][C@H:8]([C:13]([NH:15][C@H:16]([C:19]([NH:21][C@H:22]([C:26]([NH:28][C@H:29]([C:34]([NH:36][C@H:37]([C:42]([NH:44][C@H:45]([C:51]([NH:53][C@H:54]([C:60]([NH:62][C@H:63]([C:66]([NH:68][C@H:69]([C:74]([NH:76][C@H:77]([C:85]([NH:87][C@H:88]([C:91]([NH:93][C@H:94]([C:110]([NH:112][C@H:113]([C:119]([OH:121])=[O:120])[CH2:114][CH2:115][C:116](=[O:117])[OH:118])=[O:111])[CH2:95][CH2:96][CH2:97][CH2:98][NH2:99])=[O:92])[CH2:89][OH:90])=[O:86])[CH2:78][CH2:79][CH2:80][NH:81][C:82](=[NH:83])[NH2:84])=[O:75])[CH2:70][CH:71]([CH3:72])[CH3:73])=[O:67])[CH2:64][OH:65])=[O:61])[CH2:55][CH2:56][C:57](=[O:58])[OH:59])=[O:52])[CH2:46][CH2:47][C:48](=[O:50])[NH2:49])=[O:43])[CH2:38][CH:39]([CH3:40])[CH3:41])=[O:35])[CH2:30][C:31](=[O:33])[NH2:32])=[O:27])[C@@H:23]([CH3:25])[OH:24])=[O:20])[CH2:17][OH:18])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH2:3][OH:4]

Participants

3

Reactant 1

HCID 131713875HCID 131713875, compound

Product 1

HCID 178446006HCID 178446006, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

150 Milligrams of Z-Ser-Leu-Ser-Thr-Asn-Leu-Gln-Glu-Ser-Leu-Arg-Ser-Lys(Tos)-Glu-OH was dissolved in liquid ammonia previously dried with metallic sodium, then small pieces of metallic sodium were added to the solution under stirring condition until the color of the reaction mixture is changed to blue and kept it for 30 seconds to 1 minute. Further crystals of NH4Cl were added to the reaction mixture, an excess metallic sodium was neutralized, after ammonia was removed completely by distillation at a room temperature, the reaction product was subjected to gel-filtration with Sephadex G-25 gel by using 50%-acetic acid as the eluting solvent, collecting the desired fraction and lyophilizing the desired fraction by adding water after concentration, to obtain 94 mg of the desired product (peptide of the present invention). Hereinafter, this product is referred to as [Peptide G].

Workup

  1. dry with materialpreviously dried with metallic sodium
  2. additionsmall pieces of metallic sodium were added to the solution
  3. customfor 30 seconds to 1 minute
  4. additionFurther crystals of NH4Cl were added to the reaction mixture
  5. customafter ammonia was removed completely by distillation at a room temperature
  6. filtrationthe reaction product was subjected to gel-filtration with Sephadex G-25 gel
  7. customcollecting the desired fraction
  8. additionby adding water
  9. concentrationafter concentration

Sources & evidence

ORD record
ord-39e1af5f944e423baf956153831fadce
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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