Sodium Hydroxide → [3-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-propyl]-phosphonic acid monomethyl ester

HRID 2292801Notes

Reaction equation

HRID 2292801 reaction equation
[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH2:27][CH3:28])=[C:14]2[CH2:29][C:30]([NH2:32])=[O:31])(=[O:6])[O:4]C.[OH-].[Na+]>CO.O>[CH3:1][O:2][P:3]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH2:27][CH3:28])=[C:14]2[CH2:29][C:30]([NH2:32])=[O:31])(=[O:4])[OH:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10504075[3-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-propyl]-phosphonic acid dimethyl ester

Product 1

HCID 10623151[3-(1-Benzyl-3-carbamoylmethyl-2-ethyl-1H-indol-5-yloxy)-propyl]-phosphonic acid monomethyl esterYield 77.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 162 mg (0.35 mmol) of [3-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid dimethyl ester and 5 mL of 1N NaOH in 10 mL of MeOH was heated to maintain reflux for 5 hours, diluted with water and extracted with ethyl acetate. The aqueous layer was made acidic to pH 2-3 with 1N HCl and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 120 mg (77% yield) of [3-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]propyl]phosphonic acid monomethyl ester.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 5 hours
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate solution was washed with brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-7fc9e5ecf1b84a14b80b9bc46e42ed2f
Source dataset
uspto-grants-1997_11
Patent number
US05684034

Reaction notes

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