HCID 131713878, compound → HCID 178446005, compound

HRID 1632425Notes

Reaction equation

HRID 1632425 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:11]([NH:13][C@H:14]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:31]([NH:33][C@H:34]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:63]([NH:65][C@H:66]([C:72]([NH:74][C@H:75]([C:78]([NH:80][C@H:81]([C:86]([NH:88][C@H:89]([C:97]([NH:99][C@H:100]([C:103]([NH:105][C@H:106]([C:122]([NH:124][C@H:125]([C:131]([OH:133])=[O:132])[CH2:126][CH2:127][C:128](=[O:130])[OH:129])=[O:123])[CH2:107][CH2:108][CH2:109][CH2:110][NH:111]S(C1C=CC(C)=CC=1)(=O)=O)=[O:104])[CH2:101][OH:102])=[O:98])[CH2:90][CH2:91][CH2:92][NH:93][C:94](=[NH:96])[NH2:95])=[O:87])[CH2:82][CH:83]([CH3:85])[CH3:84])=[O:79])[CH2:76][OH:77])=[O:73])[CH2:67][CH2:68][C:69](=[O:71])[OH:70])=[O:64])[CH2:58][CH2:59][C:60](=[O:62])[NH2:61])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:42][C:43](=[O:45])[NH2:44])=[O:39])[C@@H:35]([CH3:37])[OH:36])=[O:32])[CH2:29][OH:30])=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[CH2:15][OH:16])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1>N>[NH2:1][C@H:2]([C:11]([NH:13][C@H:14]([C:17]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:31]([NH:33][C@H:34]([C:38]([NH:40][C@H:41]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:63]([NH:65][C@H:66]([C:72]([NH:74][C@H:75]([C:78]([NH:80][C@H:81]([C:86]([NH:88][C@H:89]([C:97]([NH:99][C@H:100]([C:103]([NH:105][C@H:106]([C:122]([NH:124][C@H:125]([C:131]([OH:133])=[O:132])[CH2:126][CH2:127][C:128](=[O:129])[OH:130])=[O:123])[CH2:107][CH2:108][CH2:109][CH2:110][NH2:111])=[O:104])[CH2:101][OH:102])=[O:98])[CH2:90][CH2:91][CH2:92][NH:93][C:94](=[NH:95])[NH2:96])=[O:87])[CH2:82][CH:83]([CH3:85])[CH3:84])=[O:79])[CH2:76][OH:77])=[O:73])[CH2:67][CH2:68][C:69](=[O:70])[OH:71])=[O:64])[CH2:58][CH2:59][C:60](=[O:62])[NH2:61])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:42][C:43](=[O:45])[NH2:44])=[O:39])[C@@H:35]([CH3:37])[OH:36])=[O:32])[CH2:29][OH:30])=[O:26])[CH2:21][CH:22]([CH3:23])[CH3:24])=[O:18])[CH2:15][OH:16])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 131713878HCID 131713878, compound

Product 1

HCID 178446005HCID 178446005, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

Z-Tyr-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 with stirring 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 to neutralize an excess metallic sodium, after ammonia was completely removed 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 to obtain 33 mg of the desired product. Hereinafter, this product is referred to as [Peptide H].

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 completely removed by distillation at a room temperature
  6. filtrationthe reaction product was subjected to gel-filtration with Sephadex G-25 gel

Sources & evidence

ORD record
ord-e9337ea15efa496a821a87724e2b0878
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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