Benzaldehyde → (s)-4Fluoro-alpha-[(phenylmethyl)amino]benzeneacetate sodium salt

HRID 363136

Reaction equation

[NH2:1][C@@H:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+:22]>[Pd]>[Na+:22].[F:12][C:9]1[CH:10]=[CH:11][C:6]([C@H:2]([NH:1][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]([O-:5])=[O:4])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A solution of (S)-α-amino-4-fluorobenzeneacetic acid (1.00 kg, 5.91 moles) in aqueous sodium hydroxide (1M, 5.91 L) was filtered and added to 10% palladium-on-carbon (25 g). A solution of benzaldehyde (941 g, 8.87 moles) was added and the batch was stirred under hydrogen (50 psi) for 4 hours. The batch was filtered and the filtrate was evaporated to residue under vacuum, then flushed with ethanol (2×3 L). The residue was slurried in boiling ethanol (1.5 L), then cooled to 15° C. The slurry was filtered and the filter cake was washed with cold ethanol (2×500 mL), then dried under vacuum at 55° C. to give 1.83 kg (92% yield) of (S)-4-fluoro-α-[(phenylmethyl)-amino]benzeneacetate sodium salt.

Workup

filtrationThe batch was filtered
customthe filtrate was evaporated to residue under vacuum
customflushed with ethanol (2×3 L)
filtrationThe slurry was filtered
washthe filter cake was washed with cold ethanol (2×500 mL)
customdried under vacuum at 55° C.

Sources & evidence

ORD record: ord-887564dee63f486b88751a1dbada790d
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05872116

Linked notes

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