Methanol → HCID 18369040, compound

HRID 380069Notes

Reaction equation

HRID 380069 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[K].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:22]([C:24]([O-:26])=[O:25])[NH2:23].[Na+].CO>COCCOC.Cl>[C:8]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:16]=2)([C:24]([OH:26])=[O:25])[NH2:23])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 70017DiphenylphosphineHCID 5462222PotassiumHCID 23674675HCID 23674675, compound

Product 1

HCID 18369040HCID 18369040, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 3.07 g (16.5 mmol) of diphenylphosphine in 60 ml of 1,2-dimethoxyethane was admixed with 0.64 g (16.5 mmol) of potassium. After the metallation reaction was complete, 3.0 g (15.7 mmol) of sodium 2-(2-fluorophenyl)glycinate were added and the reaction mixture was heated at 80° C. for 3 hours. Subsequently, 10 ml of methanol were added and the volatile constituents were removed at 80° C. at a pressure of 10−2 bar. The residue obtained was suspended in 500 ml of dilute aqueous hydrochloric acid (pH=4) and filtered, and then dried at 20° C. and 10−2 bar. The yield was 4.7 g (89%). For the further work-up, the product was recrystallized from a 3:1 mixture of water and methanol. The 1H, 13C{1H} and 31P{1H} NMR spectra were recorded on a Bruker AC 250 spectrometer; the mass spectra were recorded on a Varian MAT 311 A instrument.

Workup

  1. customAfter the metallation reaction
  2. customthe volatile constituents were removed at 80° C. at a pressure of 10−2 bar
  3. customThe residue obtained
  4. filtrationfiltered
  5. customdried at 20° C.
  6. customFor the further work-up, the product was recrystallized from a 3:1 mixture of water and methanol

Sources & evidence

ORD record
ord-a2ef8361f11a462bbb846de5ecba3dc4
Source dataset
uspto-grants-2001_10
Patent number
US06300517B1

Reaction notes

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