Lithium Hydroxide → 2-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid

HRID 905359Notes

Reaction equation

HRID 905359 reaction equation
[CH2:1]([O:3][P:4]([O:21][CH2:22][CH3:23])([CH:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[C:7]([O:9]CC)=[O:8])=[O:5])[CH3:2].[OH-].[Li+].C1CCC(NC2CCCCC2)CC1>CCOCC.C(OC(=O)C)C>[CH2:22]([O:21][P:4]([O:3][CH2:1][CH3:2])([CH:6]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)[C:7]([OH:9])=[O:8])=[O:5])[CH3:23]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 7582DicyclohexylamineHCID 270092Ethyl 2-diethoxyphosphoryl-3-(4-methoxyphenyl)propanoate

Product 1

HCID 131383212-(Diethoxyphosphinyl)-3-(4-methoxyphenyl)propionic acid

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

The product of stage (a) (10 g) was stirred for 4 hr with 1 M lithium hydroxide (30.5 ml). The mixture was extracted with ether, the aqueous phase cooled to 0° C. and acidified to pH 1.0 with 2 N.HCl and extracted with ethyl acetate, exhaustively. The extracts were dried after washing with brine to give a solid residue. The solid was dissolved in a mixture of ether (35 ml) and ethylacetate (35 ml) and DCHA (4.37 g) added. After refrigeration, the precipitated DCHA salt (m.p. 136°-140°) was filtered and washed with ether. The salt was partitioned between ethyl acetate and 5% citric acid solution, the ethyl acetate extract washed with brine and evaporated in vacuo to give the desired product as a crystalline solid m.p. 94°-98° C.

Workup

  1. extractionThe mixture was extracted with ether
  2. extractionHCl and extracted with ethyl acetate
  3. customThe extracts were dried
  4. washafter washing with brine
  5. customto give a solid residue
  6. additionadded
  7. filtrationAfter refrigeration, the precipitated DCHA salt (m.p. 136°-140°) was filtered
  8. washwashed with ether
  9. customThe salt was partitioned between ethyl acetate and 5% citric acid solution
  10. extractionthe ethyl acetate extract
  11. washwashed with brine
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-39f130dd2f674227a63169a291aed60d
Source dataset
uspto-grants-1983_12
Patent number
US04423242

Reaction notes

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