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

HRID 1797446
Notes
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Reaction equation

HRID 1797446 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10268322Ethyl 3-[(diethoxymethyl)(ethoxy)phosphoryl]-2-fluorobutanoate

Product 1

HCID 9857454Ethyl 3-amino-2-fluoro-1-methyl-3-oxopropyl(diethoxymethyl)phosphinateYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

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

  1. customevaporated

Sources & evidence

ORD record
ord-a4ea2073a7764210866c75d4190e2cec
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07034176B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes