Potassium Carbonate → HCID 53658361, compound

HRID 1857549Notes

Reaction equation

HRID 1857549 reaction equation
[CH3:1][O:2][P:3]([CH2:19][CH:20]([C:25](=[O:41])[NH:26][CH:27]([C:37](=[O:40])[NH:38][CH3:39])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12]C(=O)C(F)(F)F)[CH:7]=1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CO>[CH3:1][O:2][P:3]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1)([CH2:19][CH:20]([C:25](=[O:41])[NH:26][CH:27]([C:37](=[O:40])[NH:38][CH3:39])[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 53754061HCID 53754061, compound

Product 1

HCID 53658361HCID 53658361, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

{2-[2-(4-Methoxyphenyl)-1-methylcarbamoylethylcarbamoyl]-4-methyl-pentyl}-[3-(2,2,2-trifluoroacetylamino)benzyl]phosphinic acid methyl ester (prepared from the appropriate starting materials using the procedures described in Example 2/Steps A-D) (105 mg, 0.18 mmole) was treated with potassium carbonate (242 mg, 1.75 mmole) in 10% aqueous methanol (10 ml) for 18 hours. 1N Sodium hydroxide (1 ml) was added and after 3 hours the reaction mixture was concentrated and ethyl acetate (25 ml) and water (5 ml) added. The ethyl acetate layer was removed and the water extracted with ethyl acetate (3×20 ml). The combined ethyl acetate extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated to give 56 mg (64%) of (3-aminobenzyl){2-[2-(4-methoxy phenyl)-1-methylcarbamoylethyl carbamoyl]-4-methylpentyl}phosphinic acid methyl ester as a light yellow oil.

Workup

  1. concentrationwas concentrated
  2. additionethyl acetate (25 ml) and water (5 ml) added
  3. customThe ethyl acetate layer was removed
  4. extractionthe water extracted with ethyl acetate (3×20 ml)
  5. dry with materialThe combined ethyl acetate extracts were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0046acc61f1b444cb34e6e0202a598f8
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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