Trifluoroacetic acid → HCID 20223100, compound
Reaction equation
[C:1]([CH:6]([NH:15][NH:16]C(OC(C)(C)C)=O)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O:3][CH2:4][CH3:5])=[O:2].[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27]>>[F:24][C:25]([F:30])([F:29])[C:26]([OH:28])=[O:27].[C:9]1([CH2:8][CH2:7][CH:6]([NH:15][NH2:16])[C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1Participants
Procedure
A solution of ethyl 4-phenyl-2-oxobutanoate (2.06 g; 10 mmol) and t-butylcarbazate (1.32 g; 10 mmol) in THF (50 ml) can be warmed at reflux for 8 hours. Solvent can be evaporated and the residue taken up in anhydrous ethanol (25 ml). Sodium cyanoborohydride (0.31 g; 5 mmol) can be added, and the solution stirred for 4 hrs. The residue, after evaporation, can be stirred with EtOAc (50 ml) and hydrochloric acid (0.5 N: 20 ml) for 30 minutes. The aqueous layer can be neutralized by addition of K2CO3 and extracted with EtOAc (3×25 ml). The combined organic portions can be washed with H2O and brine and dried (MgSO4). The residue, upon evaporation, can be purified by chromatography on silica gel, affording N-(1-carboethoxy-3-phenylpropyl)-N'-BOC-hydrazine. An ice-cold solution of the above hydrazine in trifluoroacetic acid can be allowed to stand for 1 hr. Removal of solvent can provide hydrazine (56) as the trifluoroacetic acid salt.
Workup
- customRemoval of solvent
Sources & evidence
- ORD record
- ord-7320e43838f8412f92dd4f5d555228bc
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04634715
Reaction notes
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