Isoamyl Nitrite → Z-Ser-Ser-Ome

HRID 1632426Notes

Reaction equation

HRID 1632426 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:38]([O:40][CH3:41])=[O:39])[CH2:36][OH:37].Cl>CN(C)C=O.Cl.O1CCOCC1>[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:38]([O:40][CH3:41])=[O:39])[CH2:36][OH:37])=[O:6])[CH2:3][OH:4]

Participants

7

Reactant 4

HCID 8053Isoamyl NitriteHCID 8471Triethylamine2×HCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 7016357(S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate

Product 1

HCID 11809968Z-Ser-Ser-Ome

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 204431481,4-Dioxane hydrochlorideSolvent

Conditions

Temperature
-15 °C

Procedure

5.06 Grams of Z-Ser-NHNH2 was dissolved in 50 ml of dimethylformamide with 6.66 ml of 6N-hydrochloric acid/dioxane, the solution was cooled to -15° C. then 2.68 ml of isoamyl nitrite was added thereto, and the mixture was stirred for 5 minutes. Next, 5.60 ml of triethylamine was added to neutralize the reaction mixture. This reaction mixture was added to 30 ml of dimethylformamide solution containing 3.11 g of H-Ser-OMe.HCl and 2.80 ml of triethylamine, then this mixture was stirred at 4° C. for 20 hours. Dimethylformamide was removed by distillation, the residue obtained was extracted with ethyl acetate, the extract was washed with water and was dried with anhydrous sodium sulfate. After removal of ethyl acetate by distillation, the residue was crystallized by adding ether, reprecipitated from ethyl acetate-ether to obtain 3.75 g of Z-Ser-Ser-OMe.

Workup

  1. stirringthis mixture was stirred at 4° C. for 20 hours
  2. customDimethylformamide was removed by distillation
  3. customthe residue obtained
  4. extractionwas extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. customAfter removal of ethyl acetate
  8. distillationby distillation
  9. customthe residue was crystallized
  10. additionby adding ether
  11. customreprecipitated from ethyl acetate-ether

Sources & evidence

ORD record
ord-7f96a65184eb4633ab8d60057ff904cb
Source dataset
uspto-grants-1984_10
Patent number
US04474754

Reaction notes

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