Hydrochloric Acid → Ethyl 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylate monohydrochloride

HRID 1943008Notes

Reaction equation

HRID 1943008 reaction equation
C(OC([N:8]([C:17]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23])[NH:9]C(OC(C)(C)C)=O)=O)(C)(C)C.[ClH:29]>C(OCC)(=O)C>[ClH:29].[NH:8]([C:17]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:21][C:20](=[O:22])[NH:19][C:18]1=[O:23])[NH2:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67342586ethyl 3-[N,N'-bis(tert-butyloxycarbonyl)hydrazino]-2,5-dioxopyrrolidine-3-carboxylate

Product 1

HCID 66992526Ethyl 3-hydrazino-2,5-dioxopyrrolidine-3-carboxylate monohydrochlorideYield 76%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the compound of Example 4 (5.77 g) in ethyl acetate (20 ml) was added a solution of 4M hydrogen chloride in ethyl acetate (25 ml) and the mixture was stirred at room temperature for 24 hours. The resulting precipitates were collected by filtering and washed with ethyl acetate to give the desired product (3.02 g, 76%) as powder. The desired product was identified to be a monohydrochloride salt thereof by the results of elementary analysis and X-ray crystallographic analysis. Melting point: 189-190° C. (decomposition). 1H NMR (300 MHz, DMSO-d6, 25° C.) δ: 12.1 (1H, br), 9.58 (3H, br), 4.23 (2H, q, J=7.0 Hz), 3.15 (2H, s), 1.22 (3H, t, J=7.1 Hz). Elementary analysis: Calculated for C7H12ClN3O4: C, 35.38; H, 5.09; Cl, 14.92; N, 17.68. Founded: C, 35.28; H, 5.02; Cl, 14.83; N, 17.68.

Workup

  1. customThe resulting precipitates
  2. customwere collected
  3. filtrationby filtering
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-7af209508a474329be65b5a7dd5b83c9
Source dataset
uspto-grants-2013_03
Patent number
US08389742B2

Reaction notes

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