Dimethyl methylphosphonate → 1,1-Difluoro-3-amino-3-hydroxymethyl-5-(4-octylphenyl)pentylphosphonic acid

HRID 2304993Notes

Reaction equation

[NH2:1][C:2]([CH2:21]O)([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)[CH2:3][OH:4].[Li].C([Li])CCC.[F:29][CH:30]([P:32](=[O:39])([O:36]CC)[O:33]CC)[F:31].CP(=O)(OC)OC>>[F:29][C:30]([P:32](=[O:33])([OH:39])[OH:36])([F:31])[CH2:21][C:2]([NH2:1])([CH2:3][OH:4])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1

Participants

Reactant 5

HCID 12958Dimethyl methylphosphonate

HCID 107970Fingolimod

HCID 2758305Phosphonic acid, (difluoromethyl)-, diethyl ester

HCID 3028194Lithium

HCID 178418339Butyllithium

Product 1

HCID 102023641,1-Difluoro-3-amino-3-hydroxymethyl-5-(4-octylphenyl)pentylphosphonic acid

Procedure

The title compound was prepared from 2-amino-2-hydroxymethyl-4-(4-(octyl)phenyl)butanol (FrY 720) using procedures analogous to those described in EXAMPLE 2, except that lithium dilsopropylamide was substituted for n-butyllithium in Step C and diethyl difluoromethylphosphonate was substituted for dimethyl methylphosphonate in Step C: Mass spectrum (NH3—CI) 422 (M+H).

Sources & evidence

ORD record: ord-d345444460274bfca6870ab5e5a72191
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06437165B1

Reaction notes

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