Isoamyl Nitrite → Z-Ser-Leu-Gly-OC2H5

HRID 1632394Notes

Reaction equation

HRID 1632394 reaction equation
[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:5]([NH:7]N)=[O:6])[CH2:3][OH:4].N(OCCC(C)C)=O.C(N(CC)CC)C.N[C@H:35]([C:40]([NH:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:41])[CH2:36][CH:37]([CH3:39])[CH3:38]>CN(C)C=O>[NH:1]([C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C@H:2]([C:5]([NH:7][C@H:35]([C:40]([NH:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:41])[CH2:36][CH:37]([CH3:39])[CH3:38])=[O:6])[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 8053Isoamyl NitriteHCID 8471Triethylamine2×HCID 7016357(S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamateHCID 11390304H-Leu-Gly-Oet

Product 1

HCID 131713843Z-Ser-Leu-Gly-OC2H5

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2.48 Grams of Z-Ser-NHNH2 was dissolved in 20 ml of dimethylformamide and 4.89 ml of N-hydrochloric acid/dioxane, after cooled the reaction mixture to -15° C., then 1.31 ml of isoamyl nitrite was added thereto and stirred for 5 minutes. Then 4.11 ml of triethylamine was added to the reaction mixture to neutralize the mixture. This reaction mixture was added into 10 ml of a dimethylformamide solution containing the above-mentioned H-Leu-Gly-OC2H5 and 1.24 ml of triethylamine and stirred at 4° C. for 20 hours. After removal of dimethylformamide by distillation, the residue thus obtained was extracted with ethyl acetate, and the extract was washed with 1N-citric acid and a saturated aqueous solution of sodium chloride in this order, then the extract was dried with anhydrous magnesium sulfate. After removal of ethyl acetate, reprecipitated from ethyl acetate to obtain 2.64 g of Z-Ser-Leu-Gly-OC2H5.

Workup

  1. stirringstirred at 4° C. for 20 hours
  2. customAfter removal of dimethylformamide
  3. distillationby distillation
  4. customthe residue thus obtained
  5. extractionwas extracted with ethyl acetate
  6. washthe extract was washed with 1N-citric acid
  7. dry with materiala saturated aqueous solution of sodium chloride in this order, then the extract was dried with anhydrous magnesium sulfate
  8. customAfter removal of ethyl acetate
  9. customreprecipitated from ethyl acetate

Sources & evidence

ORD record
ord-127248fbbfae456ba7b9d69ae84c653a
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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