Ethyl 2-(benzyl((diethoxyphosphoryl)methyl)amino)acetate → Ethyl 2-((diethoxyphosphoryl)methylamino)acetate

HRID 870140Notes

Reaction equation

C([N:8]([CH2:15][P:16]([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])C1C=CC=CC=1>C(O)C.C(O)(=O)C.[Pd]>[CH2:22]([O:21][P:16]([CH2:15][NH:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])([O:18][CH2:19][CH3:20])=[O:17])[CH3:23]

Participants

Conditions

Temperature: 50 °C

Procedure

A 250-mL pressure tank reactor was purged, flushed and maintained with a hydrogen atmosphere, then, was added a solution of ethyl 2-(benzyl((diethoxyphosphoryl)methyl)amino)acetate (8.0 g, 23.32 mmol, 1.00 equiv) in ethanol (180 mL), acetic acid (10 mL), Pd/C (0.9 g). The resulting solution was stirred at 20 atm for 32 h at 50° C. The solids were filtered out, and the resulting mixture was concentrated under vacuum. This resulted in 6.0 g (82%) of the acetic acid salt of ethyl 2-((diethoxyphosphoryl)methylamino)acetate as a brown oil.

Workup

customA 250-mL pressure tank reactor was purged
customflushed
temperaturemaintained with a hydrogen atmosphere
filtrationThe solids were filtered out
concentrationthe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record: ord-434909458c6844a78bd4fe97d669452a
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969377B2

Reaction notes

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