Isoamyl Nitrite → HCID 178427530, compound

HRID 1632434Notes

Reaction equation

HRID 1632434 reaction equation
[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13]N)=[O:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].N(OCCC(C)C)=O.N[C@H:34]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:59]([NH:61][C@H:62]([C:80]([NH:82][C@H:83]([C:86]([NH:88][C@H:89]([C:92]([OH:94])=[O:93])[CH2:90][OH:91])=[O:87])[CH2:84][OH:85])=[O:81])[CH2:63][CH2:64][CH2:65][NH:66][C:67](=[NH:79])[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:60])[CH2:54][CH2:55][C:56](=[O:58])[NH2:57])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.N(C(OCC1C=CC=CC=1)=O)[C@H](C(NCC(N=[N+]=[N-])=O)=O)CC(C)C>CN(C)C=O.Cl.O1CCOCC1.C(N(CC)CC)C>[NH:1]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[C@H:2]([C:7]([NH:9][CH2:10][C:11]([NH:13][C@H:34]([C:42]([NH:44][C@H:45]([C:50]([NH:52][C@H:53]([C:59]([NH:61][C@H:62]([C:80]([NH:82][C@H:83]([C:86]([NH:88][C@H:89]([C:92]([OH:94])=[O:93])[CH2:90][OH:91])=[O:87])[CH2:84][OH:85])=[O:81])[CH2:63][CH2:64][CH2:65][NH:66][C:67](=[NH:79])[NH:68][S:69]([C:72]1[CH:73]=[CH:74][C:75]([CH3:76])=[CH:77][CH:78]=1)(=[O:71])=[O:70])=[O:60])[CH2:54][CH2:55][C:56](=[O:58])[NH2:57])=[O:51])[CH2:46][CH:47]([CH3:48])[CH3:49])=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:12])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 8053Isoamyl NitriteHCID 131713890HCID 131713890, compoundHCID 131713892HCID 131713892, compoundHCID 178427532HCID 178427532, compound

Product 1

HCID 178427530HCID 178427530, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

0.39 Gram of Z-Leu-Gly-NHNH2 was dissolved in 5 ml of dimethylformamide and 0.58 ml of 6N HCl/dioxane, then a reaction similar to that described in Reference example 1 was carried out by using 10 ml of a dimethylformamide solution containing 0.15 ml of isoamyl nitrite, 0.49 ml of triethylamine and 1.00 g of H-Phe-Leu-Gln-Arg(Tos)-Ser-Ser-OH, further an equivalent amount of Z-Leu-Gly-N3 was added to the reaction mixture and reacted at 4° C. for 20 hours. The reaction mixture was extracted with butanol, the extract was washed with 2%-acetic acid, then butanol and acetic acid were removed by sistillation, the residue was crystallized from ether. The crystals were collected by filtration and washed with a hot methanol to obtain 0.65 g of Z-Leu-Gly-Phe-Leu-Gln-Arg(Tos)-Ser-Ser-OH.

Workup

  1. customreacted at 4° C. for 20 hours
  2. extractionThe reaction mixture was extracted with butanol
  3. washthe extract was washed with 2%-acetic acid
  4. custombutanol and acetic acid were removed by sistillation
  5. customthe residue was crystallized from ether
  6. filtrationThe crystals were collected by filtration
  7. washwashed with a hot methanol

Sources & evidence

ORD record
ord-0c13fa23f5544eac96413fd774babaa3
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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