Water → tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate

HRID 1497513Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH2:7][N:8]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([O-])=O.O.[Cl-].[NH4+]>[Fe].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][CH:25]=1)[CH2:7][N:8]([C:17](=[O:22])[C:18]([F:19])([F:20])[F:21])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of tert-butyl N-(3-nitrobenzyl)-N-(trifluoroacetyl)glycinate (4.30 g), iron (13.2 g), water (41.8 mL), and ethanol (83.5 mL) was added ammonium chloride (2.54 g) at room temperature, followed by heating and refluxing at 100° C. for 1 hour. After leaving to be cooled, the reaction suspension was filtered through Celite and the filtrate was concentrated under reduced pressure. To the residue was added water, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate (3.76 g).

Workup

temperatureby heating
customAfter leaving
temperatureto be cooled
filtrationthe reaction suspension was filtered through Celite
concentrationthe filtrate was concentrated under reduced pressure
additionTo the residue was added water
extractionfollowed by extraction with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-54e942401d114f45894eeed1fd7fb226
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199927B2

Reaction notes

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