Acetohydrazide → HCID 90192609, compound

HRID 923512Notes

Reaction equation

HRID 923512 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@:12]([CH3:16])([C:13]([OH:15])=O)[CH2:11][O:10][C:9]1([CH3:18])[CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:19]([NH:22][NH2:23])(=[O:21])[CH3:20].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>O.CN(C=O)C>[C:19]([NH:22][NH:23][C:13]([C@:12]1([CH3:16])[CH2:11][O:10][C:9]([CH3:18])([CH3:17])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15])(=[O:21])[CH3:20]

Participants

8

Reactant 5

HCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21356182HCID 21356182, compound

Product 1

HCID 90192609HCID 90192609, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1.00 g of (4S)-3-(tert-butoxycarbonyl)-2,2,4-trimethyl-1,3-oxazolidine-4-carboxylic acid, 400 mg of acetohydrazide, 850 mg of 1-hydroxybenzotriazole, 2.0 ml of diisopropylethylamine, and 20 ml of DMF was added 1.2 g of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride, followed by stirring at room temperature for 5 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate, and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 1.11 g of tert-butyl (4S)-4-[(2-acetylhydrazino)carbonyl]-2,2,4-trimethyl-1,3-oxazolidine-3-carboxylate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  4. customthe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2bf3d93d581449daa79ee8167466b5b5
Source dataset
uspto-grants-2016_03
Patent number
US09278968B2

Reaction notes

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