Isoamyl Nitrite → HCID 178427448, compound

HRID 1632409Notes

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:5]([NH:7][C@H:8]([C:13]([NH:15]N)=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH2:3][OH:4].Cl.O1CCOCC1.N(OCCC(C)C)=O.[N-]=[N+]=[N-].N[C@H:46]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:79]([NH:81][C@H:82]([C:88]([OH:90])=[O:89])[CH2:83][CH2:84][C:85](=[O:87])[OH:86])=[O:80])[CH2:64][CH2:65][CH2:66][CH2:67][NH:68][S:69]([C:72]1[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=1)(=[O:71])=[O:70])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:47][CH2:48][CH2:49][NH:50][C:51](=[NH:53])[NH2:52]>CN(C)C=O.C(N(CC)CC)C>[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:5]([NH:7][C@H:8]([C:13]([NH:15][C@H:46]([C:54]([NH:56][C@H:57]([C:60]([NH:62][C@H:63]([C:79]([NH:81][C@H:82]([C:88]([OH:90])=[O:89])[CH2:83][CH2:84][C:85](=[O:86])[OH:87])=[O:80])[CH2:64][CH2:65][CH2:66][CH2:67][NH:68][S:69]([C:72]1[CH:78]=[CH:77][C:75]([CH3:76])=[CH:74][CH:73]=1)(=[O:71])=[O:70])=[O:61])[CH2:58][OH:59])=[O:55])[CH2:47][CH2:48][CH2:49][NH:50][C:51](=[NH:52])[NH2:53])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6])[CH2:3][OH:4]

Participants

Conditions

Temperature: -15 °C

Procedure

1.03 Grams of Z-Ser-Leu-NHNH2 was dissolved in 15 ml of dimethylformamide, then 1.41 ml of 6N-hydrochloric acid/dioxane was further added thereto, and the mixture was cooled to -15° C., then 0.38 ml of isoamyl nitrite was added under a stirring condition. After the reaction mixture shows a negative reaction in hydrazide test, then a cold solution of 0.40 ml of dimethylformamide with 1.18 ml of triethylamine was added drop by drop in small amounts to neutralize the reaction mixture. This reaction mixture containing the azide was added to 10 ml of a cold dimethylformamide solution containing H-Arg-Ser-Lys(Tos)-Glu-OH obtained in the above-mentioned step 5(a) and 0.66 ml of triethylamine, then whole mixture was stirred at -10° to -15° C. for 2 hours, and at 4° C. for 20 hours. Dimethylformamide was removed by distillation under a reduced pressure and the residue thus obtained was extracted with n-butanol saturated with water and the butanol layer was wahsed 5 times with water being saturated with n-butanol and the solvent was removed by distillation. The residue was solidified by adding ethyl ether, and reprecipitated from methanol-ethyl acetate to obtain 1.92 g of the desired product.

Workup

waitat 4° C. for 20 hours
customDimethylformamide was removed by distillation under a reduced pressure
customthe residue thus obtained
extractionwas extracted with n-butanol saturated with water
customthe solvent was removed by distillation
additionby adding ethyl ether
customreprecipitated from methanol-ethyl acetate

Sources & evidence

ORD record: ord-df1276c653bf4bad8fe520157c35c0d3
Source dataset: uspto-grants-1984_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04474754

Reaction notes

Loading…