Phthalic Anhydride → HCID 178445559, compound

HRID 1857548Notes

Reaction equation

HRID 1857548 reaction equation
[CH2:1]([O:8][C:9](=[O:28])[CH:10]([CH2:15][PH:16]([O:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]1(=O)[O:34][C:32](=[O:33])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12>C(O)(=O)C>[CH2:1]([O:8][C:9](=[O:28])[CH:10]([CH2:15][PH:16]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([N:27]2[C:32](=[O:33])[C:31]3[C:30](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:29]2=[O:34])=[CH:25][CH:26]=1)=[O:17])[CH2:11][CH:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 178445560HCID 178445560, compound

Product 1

HCID 178445559HCID 178445559, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-[(4-Aminobenzyl)methoxyphosphinoylmethyl]-4-methylpentanoic acid benzyl ester (prepared as described in Example 2/Step A) (242 mg, 0.60 mmole) and phthalic anhydride (133 mg, 0.90 mmole) in acetic acid (10 ml) were refluxed for 1 hour. The cooled reaction mixture was concentrated and the residue dissolved in ethyl acetate (100 ml). This solution was washed with saturated sodium bicarbonate solution (3×20 ml) and dried with magnesium sulfate. Filtration and concentration gave a light yellow oil which was purified by chromatography (ethyl acetate) yielding 162 mg (51%) of 2-{[4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)benzyl]methoxyphosphinoyl methyl}-4-methylpentanoic acid benzyl ester as a yellow solid.

Workup

  1. customwere refluxed for 1 hour
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated
  4. dissolutionthe residue dissolved in ethyl acetate (100 ml)
  5. washThis solution was washed with saturated sodium bicarbonate solution (3×20 ml)
  6. dry with materialdried with magnesium sulfate
  7. filtrationFiltration and concentration
  8. customgave a light yellow oil which
  9. customwas purified by chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-3192b73281bd45ffbf357123d6c0a7d2
Source dataset
uspto-grants-2000_11
Patent number
US06147061

Reaction notes

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