HCID 178427446, compound → HCID 178446004, compound

HRID 1632417Notes

Reaction equation

HRID 1632417 reaction equation
[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH:24][C@H:25]([C:31]([NH:33][C@H:34]([C:40]([NH:42][C@H:43]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:65]([NH:67][C@H:68]([C:71]([NH:73][C@H:74]([C:90]([NH:92][C@H:93]([C:99]([OH:101])=[O:100])[CH2:94][CH2:95][C:96](=[O:98])[OH:97])=[O:91])[CH2:75][CH2:76][CH2:77][CH2:78][NH:79]S(C1C=CC(C)=CC=1)(=O)=O)=[O:72])[CH2:69][OH:70])=[O:66])[CH2:58][CH2:59][CH2:60][NH:61][C:62](=[NH:64])[NH2:63])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:44][OH:45])=[O:41])[CH2:35][CH2:36][C:37](=[O:39])[OH:38])=[O:32])[CH2:26][CH2:27][C:28](=[O:30])[NH2:29])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:7])[C@@H:3]([CH3:5])[OH:4]>N>[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@H:17]([C:22]([NH:24][C@H:25]([C:31]([NH:33][C@H:34]([C:40]([NH:42][C@H:43]([C:46]([NH:48][C@H:49]([C:54]([NH:56][C@H:57]([C:65]([NH:67][C@H:68]([C:71]([NH:73][C@H:74]([C:90]([NH:92][C@H:93]([C:99]([OH:101])=[O:100])[CH2:94][CH2:95][C:96](=[O:97])[OH:98])=[O:91])[CH2:75][CH2:76][CH2:77][CH2:78][NH2:79])=[O:72])[CH2:69][OH:70])=[O:66])[CH2:58][CH2:59][CH2:60][NH:61][C:62](=[NH:63])[NH2:64])=[O:55])[CH2:50][CH:51]([CH3:53])[CH3:52])=[O:47])[CH2:44][OH:45])=[O:41])[CH2:35][CH2:36][C:37](=[O:38])[OH:39])=[O:32])[CH2:26][CH2:27][C:28](=[O:30])[NH2:29])=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:7])[C@@H:3]([CH3:5])[OH:4]

Participants

3

Reactant 1

HCID 178427446HCID 178427446, compound

Product 1

HCID 178446004HCID 178446004, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

51.0 Milligrams of H-Thr-Asn-Leu-Gln-Glu-Ser-Leu-Arg-Ser-Lys(Tos)-Glu-OH was dissolved in liquid ammonia being dried with metallic sodium previously, 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 completely removed by distillation at a room temperature, the readtion product was subjected to gel-filtration with Sephadex G-25 gel by using 50%-acetic acid as the eluting solvent, for collecting the desired fraction, and the lyophilizing the raction by adding water after concentration, to obtain 32 mg of the desired product (peptide of the present invention). Hereinafter, this product is referred to as [Peptide F].

Workup

  1. dry with materialdried with metallic sodium previously
  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 readtion product was subjected to gel-filtration with Sephadex G-25 gel
  7. customfor collecting the desired fraction
  8. additionthe lyophilizing the raction by adding water
  9. concentrationafter concentration

Sources & evidence

ORD record
ord-249584c4708b463495b75c5732741a7a
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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