Isoamyl Nitrite → Azide

HRID 1632436Notes

Reaction equation

[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:7]([NH:9][C@H:10]([C:13]([NH:15][NH2:16])=[O:14])[CH2:11][OH:12])=[O:8])[CH2:3][CH2:4][S:5][CH3:6].Cl.O1CCOCC1.[N:34](OCCC(C)C)=O.[NH2:42][C@H:43]([C:52]([NH:54][C@H:55]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:76]([NH:78][CH2:79][C:80]([NH:82][C@H:83]([C:91]([NH:93][C@H:94]([C:99]([NH:101][C@H:102]([C:108]([NH:110][C@H:111]([C:129]([NH:131][C@H:132]([C:135]([NH:137][C@H:138]([C:141]([OH:143])=[O:142])[CH2:139][OH:140])=[O:136])[CH2:133][OH:134])=[O:130])[CH2:112][CH2:113][CH2:114][NH:115][C:116](=[NH:128])[NH:117][S:118]([C:121]1[CH:127]=[CH:126][C:124]([CH3:125])=[CH:123][CH:122]=1)(=[O:120])=[O:119])=[O:109])[CH2:103][CH2:104][C:105](=[O:107])[NH2:106])=[O:100])[CH2:95][CH:96]([CH3:98])[CH3:97])=[O:92])[CH2:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)=[O:81])=[O:77])[CH2:72][CH:73]([CH3:75])[CH3:74])=[O:69])[CH2:64][CH:65]([CH3:67])[CH3:66])=[O:61])[CH2:56][C:57](=[O:59])[NH2:58])=[O:53])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1>CN(C)C=O.CN(C)P(=O)(N(C)C)N(C)C.C(N(CC)CC)C>[N-:34]=[N+:15]=[N-:16].[NH:1]([C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])[C@H:2]([C:7]([NH:9][C@H:10]([C:11]([NH:42][C@H:43]([C:52]([NH:54][C@H:55]([C:60]([NH:62][C@H:63]([C:68]([NH:70][C@H:71]([C:76]([NH:78][CH2:79][C:80]([NH:82][C@H:83]([C:91]([NH:93][C@H:94]([C:99]([NH:101][C@H:102]([C:108]([NH:110][C@H:111]([C:129]([NH:131][C@H:132]([C:135]([NH:137][C@H:138]([C:141]([OH:143])=[O:142])[CH2:139][OH:140])=[O:136])[CH2:133][OH:134])=[O:130])[CH2:112][CH2:113][CH2:114][NH:115][C:116](=[NH:128])[NH:117][S:118]([C:121]1[CH:122]=[CH:123][C:124]([CH3:125])=[CH:126][CH:127]=1)(=[O:120])=[O:119])=[O:109])[CH2:103][CH2:104][C:105](=[O:107])[NH2:106])=[O:100])[CH2:95][CH:96]([CH3:97])[CH3:98])=[O:92])[CH2:84][C:85]1[CH:90]=[CH:89][CH:88]=[CH:87][CH:86]=1)=[O:81])=[O:77])[CH2:72][CH:73]([CH3:75])[CH3:74])=[O:69])[CH2:64][CH:65]([CH3:67])[CH3:66])=[O:61])[CH2:56][C:57](=[O:59])[NH2:58])=[O:53])[CH2:44][C:45]1[CH:46]=[CH:47][C:48]([OH:51])=[CH:49][CH:50]=1)=[O:12])[CH2:13][OH:14])=[O:8])[CH2:3][CH2:4][S:5][CH3:6]

Participants

Conditions

Temperature: 4 °C

Procedure

159 Milligrams of Z-Met-Ser-NHNH2 was dissolved in 5 ml of dimethylformamide and 0.21 ml of 6N-HCl/dioxane, then by using 0.055 ml of isoamyl nitrite and 0.17 ml of triethylamine, an azide product was prepared by a method similar to that described in Reference example 1, this reaction mixture was added to a mixture of 300 mg of H-Tyr-Asn-Leu-Leu-Gly-Phe-Leu-Gln-Arg(Tos)-Ser-Ser-OH, 5 ml of dimethylformamide and 5 ml of hexamethylphosphoric triamide, then the whole mixture was stirred at 4° C. for 24 hours. Further, 318 mg of Z-Met-Ser-NHNH2 was added thereto and stirred at 4° C. for 72 hours. By a method similar to that described in Example 4 (a), purification was conducted to obtain Z-Met-Ser-Tyr-Asn-Leu-Leu-Gly-Phe-Leu-Gln-Arg(Tos)-Ser-Ser-OH.

Workup

stirringstirred at 4° C. for 72 hours

Sources & evidence

ORD record: ord-06f75444d4444bd0a890be223c926435
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474754

Reaction notes

Loading…