Bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonate → Bis(2,2,2-trifluoroethyl)(4-amino-3-methoxybenzyl)phosphonate

HRID 1947876Notes

Reaction equation

HRID 1947876 reaction equation
OCCOP(CC1C=CC(N)=C(OC)C=1)(=O)OCCO.[F:21][C:22]([F:46])([F:45])[CH2:23][O:24][P:25]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-])=O)=[C:36]([O:43][CH3:44])[CH:35]=1)(=[O:32])[O:26][CH2:27][C:28]([F:31])([F:30])[F:29]>>[F:46][C:22]([F:21])([F:45])[CH2:23][O:24][P:25]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([NH2:40])=[C:36]([O:43][CH3:44])[CH:35]=1)(=[O:32])[O:26][CH2:27][C:28]([F:29])([F:30])[F:31]

Participants

3

Reactant 2

HCID 86654012Bis(2-hydroxyethyl)(4-amino-3-methoxybenzyl)phosphonateHCID 86654015Bis(2,2,2-trifluoroethyl)(3-methoxy-4-nitrobenzyl)phosphonate2×

Product 1

HCID 86654014Bis(2,2,2-trifluoroethyl)(4-amino-3-methoxybenzyl)phosphonateYield 77%

Procedure

The title compound was prepared according to the procedure for Compound 113A using bis(2,2,2-trifluoroethyl)(3-methoxy-4-nitrobenzyl)phosphonate (Compound 114B, 2.8 g, 6.81 mmol). The reaction mixture was filtered and the filtrate was concentrated to give the desired product (2 g, 77%). 1H NMR (DMSO-d6, 400 MHz): δ=3.29 (d, J=21.2 Hz, 2H), 3.68 (s, 3H), 4.50-4.61 (m, 4H), 4.64 (s, br, 2H), 6.50-6.60 (m, 2H), 6.67 (s, 1H).

Workup

  1. customThe title compound was prepared
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-a4d6123ae5ba47e789061948351fe382
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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