Acetohydrazide → HCID 86713161, compound

HRID 2274980Notes

Reaction equation

HRID 2274980 reaction equation
[C:1]([NH:4][NH2:5])(=[O:3])[CH3:2].[CH2:6]([O:13][N:14]1[C:20](=[O:21])[N:19]2[CH2:22][C@H:15]1[CH2:16][CH2:17][C@@H:18]2[C:23](O)=[O:24])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN=C=NCCCN(C)C.Cl.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O.O.C(Cl)(Cl)Cl.CO>[C:1]([NH:4][NH:5][C:23]([C@H:18]1[CH2:17][CH2:16][C@@H:15]2[CH2:22][N:19]1[C:20](=[O:21])[N:14]2[O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:24])(=[O:3])[CH3:2]

Participants

9

Reactant 5

HCID 14039AcetohydrazideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68761009HCID 68761009, compound

Product 1

HCID 86713161HCID 86713161, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21584188Chloroform methanolSolvent

Procedure

To a mixture of acetic acid hydrazide (1.47 gm, 19.9 mmol) and trans-6-benzyloxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (5 gm, 18.1 mmol) in N,N-dimethyl formamide (50 ml), was added EDC hydrochloride (5.19 gm, 27.1 mmol), DIPEA (9.50 ml, 54.3 mmol) and HOBt (3.66 gm, 27.1 mmol). The reaction mixture was stirred at a temperature between 25° C. to 35° C. for 14 hours. It was diluted with water (250 ml) and extracted with ethyl acetate (75 ml×3). The combined organic extract was washed with water, saturated aqueous sodium chloride solution (100 ml) and layers were separated. The organic layer was concentrated in vacuum to provide the crude compound, which was subjected for silica gel column chromatography using methanol chloroform to provide Step-1 product (2.2 gm) in 33% yield as powder.

Workup

  1. extractionextracted with ethyl acetate (75 ml×3)
  2. extractionThe combined organic extract
  3. washwas washed with water, saturated aqueous sodium chloride solution (100 ml) and layers
  4. customwere separated
  5. concentrationThe organic layer was concentrated in vacuum
  6. customto provide the crude compound, which

Sources & evidence

ORD record
ord-cd84ae6e24da411fbf8f1e78c79331e6
Source dataset
uspto-grants-2015_09
Patent number
US09127004B2

Reaction notes

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