Ammonium Hydroxide → Ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(diethoxymethyl)phosphinate

HRID 1157132Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:19][CH2:20][CH3:21])[P:5]([CH:10]([CH3:18])[CH:11]([F:17])[C:12](OCC)=[O:13])([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[OH-].[NH4+:23]>C(O)C>[NH2:23][C:12](=[O:13])[CH:11]([F:17])[CH:10]([P:5]([CH:4]([O:19][CH2:20][CH3:21])[O:3][CH2:1][CH3:2])(=[O:6])[O:7][CH2:8][CH3:9])[CH3:18]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of ethyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-2-fluorobutanoate (1.8 g, 5.5 mmol) in ethanol (3 mL) was added concentrated ammonium hydroxide (14.8 M, 0.5 mL, 7.4 mmol). The solution was stirred for 24 h at 40° C. and then evaporated to give 1.6 g (97%) of a diastereomeric mixture of ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(diethoxymethyl)phosphinate as a clear oil. 1H NMR (400 MHz, CDCl3) δ 5.7-6.7 (m, 2H), 4.9-5.5.6 (m, 1H), 4.7-4.8 (m, 1H), 4.1-4.4 (m, 2H), 3.8-4.0 (m, 4H), 2.8-3.0 (m, 1H), 1.2-1.4 (m, 12H).

Workup

customevaporated

Sources & evidence

ORD record: ord-6d70addb29f243a194604c3096baa1df
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807658B2

Reaction notes

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