Dimethylformamide → HCID 131713855, compound

HRID 1632402Notes

Reaction equation

HRID 1632402 reaction equation
CN(C)C=O.[NH2:6][C@H:7]([C:11]([NH:13][C@H:14]([C:21]([NH:23][C@H:24]([C:27]([NH:29][C@H:30]([C:35]([NH:37][CH2:38][C:39]([NH:41][C@H:42]([C:47]([NH:49][C@H:50]([C:58]([NH:60][C@H:61]([C:69]([NH:71][C@H:72]([C:74]([NH:76][C@H:77]([C:82]([NH:84][C@H:85]([C:90]([NH:92][C@H:93]([C:98]([NH:100][C@H:101]([C:106]([NH:108][C@H:109]([C:111]([NH:113][C@H:114]([C:120]([OH:122])=[O:121])[CH2:115][CH2:116][C:117](=[O:119])[NH2:118])=[O:112])[CH3:110])=[O:107])[CH2:102][CH:103]([CH3:105])[CH3:104])=[O:99])[CH2:94][CH:95]([CH3:97])[CH3:96])=[O:91])[C@H:86]([CH2:88][CH3:89])[CH3:87])=[O:83])[CH2:78][CH:79]([CH3:81])[CH3:80])=[O:75])[CH3:73])=[O:70])[CH2:62][CH2:63][CH2:64][NH:65][C:66](=[NH:68])[NH2:67])=[O:59])[CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:57])[NH2:56])=[O:48])[CH2:43][C:44](=[O:46])[NH2:45])=[O:40])=[O:36])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:28])[CH2:25][OH:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:12])[C@@H:8]([CH3:10])[OH:9].[N-]=[N+]=[N-].[NH:126](C(OCC1C=CC=CC=1)=O)[C@H:127]([C:136]([NH:138][C@H:139]([C:142]([NH:144][C@H:145]([C:150]([NH:152][C@H:153]([C:158]([N:160]1[CH2:184][CH2:183][CH2:182][C@H:161]1[C:162]([NH:164][C@H:165]([C:171](NNC(OC(C)(C)C)=O)=[O:172])[CH2:166][CH2:167][C:168](=[O:170])[NH2:169])=[O:163])=[O:159])[CH2:154][CH:155]([CH3:157])[CH3:156])=[O:151])[CH2:146][C:147](=[O:149])[OH:148])=[O:143])[CH2:140][OH:141])=[O:137])[CH2:128][C:129]1[CH:134]=[CH:133][C:132]([OH:135])=[CH:131][CH:130]=1>CN(C)P(=O)(N(C)C)N(C)C>[NH2:126][C@H:127]([C:136]([NH:138][C@H:139]([C:142]([NH:144][C@H:145]([C:150]([NH:152][C@H:153]([C:158]([N:160]1[CH2:184][CH2:183][CH2:182][C@H:161]1[C:162]([NH:164][C@H:165]([C:171]([NH:6][C@H:7]([C:11]([NH:13][C@H:14]([C:21]([NH:23][C@H:24]([C:27]([NH:29][C@H:30]([C:35]([NH:37][CH2:38][C:39]([NH:41][C@H:42]([C:47]([NH:49][C@H:50]([C:58]([NH:60][C@H:61]([C:69]([NH:71][C@H:72]([C:74]([NH:76][C@H:77]([C:82]([NH:84][C@H:85]([C:90]([NH:92][C@H:93]([C:98]([NH:100][C@H:101]([C:106]([NH:108][C@H:109]([C:111]([NH:113][C@H:114]([C:120]([OH:122])=[O:121])[CH2:115][CH2:116][C:117](=[O:119])[NH2:118])=[O:112])[CH3:110])=[O:107])[CH2:102][CH:103]([CH3:104])[CH3:105])=[O:99])[CH2:94][CH:95]([CH3:96])[CH3:97])=[O:91])[C@H:86]([CH2:88][CH3:89])[CH3:87])=[O:83])[CH2:78][CH:79]([CH3:80])[CH3:81])=[O:75])[CH3:73])=[O:70])[CH2:62][CH2:63][CH2:64][NH:65][C:66](=[NH:67])[NH2:68])=[O:59])[CH2:51][CH2:52][CH2:53][NH:54][C:55](=[NH:56])[NH2:57])=[O:48])[CH2:43][C:44](=[O:46])[NH2:45])=[O:40])=[O:36])[CH2:31][CH:32]([CH3:33])[CH3:34])=[O:28])[CH2:25][OH:26])=[O:22])[CH2:15][C:16]1[N:20]=[CH:19][NH:18][CH:17]=1)=[O:12])[C@@H:8]([CH3:10])[OH:9])=[O:172])[CH2:166][CH2:167][C:168](=[O:170])[NH2:169])=[O:163])=[O:159])[CH2:154][CH:155]([CH3:157])[CH3:156])=[O:151])[CH2:146][C:147](=[O:148])[OH:149])=[O:143])[CH2:140][OH:141])=[O:137])[CH2:128][C:129]1[CH:134]=[CH:133][C:132]([OH:135])=[CH:131][CH:130]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 33558AzideHCID 131713856HCID 131713856, compoundHCID 178455911HCID 178455911, compound

Product 1

HCID 131713855HCID 131713855, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
4 °C

Procedure

This reaction mixture was added to a solution consisting of 5 ml of a dimethylformamide solution containing 25 mg of Peptide B, i.e., H-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH, and 2 ml of hexamethylphosphoric triamide then the whole mixture was stirred at 4° C. for 20 hours. Further, an azide product of 44 mg of Z-Tyr-Ser-Asp-Leu-Pro-Gln-NHNHBoc was added to the reaction mixture and was stirred for 24 hours. The solvent was removed by distillation and the residue thus obtained was extracted with a mixture of butanol-water then crystallized from ether and the crystals were collected by filtration. Thus obtained Z-Tyr-Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH was dissolved in 30 ml of methanol and was catalytically reduced by using palladium as the catalyst. The catalyst was removed by filtration and methanol was also removed by distillation, then the residue was purified by using Sephdex G-25 (eluting solvent: 50%-acetic acid) and by using LH-20 (eluting solvent: 1/1000N-hydrochloric acid) to obtain 18 mg of H-Tyr-Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH. Hereinafter this product is referred to as [Peptide D].

Workup

  1. additionThis reaction mixture was added to a solution
  2. stirringwas stirred for 24 hours
  3. customThe solvent was removed by distillation
  4. customthe residue thus obtained
  5. extractionwas extracted with a mixture of butanol-water
  6. customthen crystallized from ether
  7. filtrationthe crystals were collected by filtration
  8. dissolutionThus obtained Z-Tyr-Ser-Asp-Leu-Pro-Gln-Thr-His-Ser-Leu-Gly-Asn-Arg-Arg-Ala-Leu-Ile-Leu-Leu-Ala-Gln-OH was dissolved in 30 ml of methanol
  9. customThe catalyst was removed by filtration and methanol
  10. customwas also removed by distillation
  11. customthe residue was purified
  12. washSephdex G-25 (eluting solvent: 50%-acetic acid)
  13. wash(eluting solvent: 1/1000N-hydrochloric acid)

Sources & evidence

ORD record
ord-a12a79e2e5ef407e8d232c64518d06fe
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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