Diisopropylethylamine → Ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate

HRID 1526512Notes

Reaction equation

HRID 1526512 reaction equation
[CH2:1]([C:8]([OH:17])([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:9](O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C(O[N:26]1[N:34]=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.ONC(=O)CCC(N)=O>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([C:8]([OH:17])([C:9]([NH:26][NH2:34])=[O:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 111283372-Benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acidHCID 18381240N-hydroxysuccinamide

Product 1

HCID 89500260Ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoateYield 133%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-3-ethoxy-2-hydroxy-3-oxopropanoic acid (250 mg), HATU (479 mg), diisopropylethyl amine (149 mg) and N-hydroxysuccinamide (145 mg) in 4 mL of DMF was stirred at ambient temperature for 1.5 h. The mixture was diluted with ethyl acetate, washed with water. The organic layer was dried with magnesium sulfate and concentrated to give the desired product ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate (352 mg), which was directly used for the next step. To ethyl 2-benzyl-3-hydrazinyl-2-hydroxy-3-oxopropanoate (352 mg) in DCM (5 mL) was added hydrazine (anhydrous, 101 mg) at ambient temperature. Instantaneously the solution turned cloudy and after 15 min the solvent was removed in vacuo to afford the crude title compound as an amorphous solid. LC/MS 275.2 (M+23).

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried with magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e2cfa20422ff4c06a93741305c96e993
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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