Phthalic Anhydride → (2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acid

HRID 622792

Reaction equation

HRID 622792 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12>C1(C)C=CC=CC=1>[CH2:7]([O:8][C:9]([CH2:11][CH2:12][C@H:13]([N:17]1[C:21](=[O:22])[C:20]2[C:19](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:18]1=[O:23])[C:14]([OH:16])=[O:15])=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 122337L-Glutamic acid, 5-(phenylmethyl) ester

Product 1

HCID 11100670(2S)-5-(Benzyloxy)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-5-oxopentanoic acidYield 60.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

16 g of L-glutamic acid γ-benzyl ester and 11 g of phthalic anhydride, both finely powdered, were stirred in 20 ml of toluene at reflux temperature for 2 hours. 50 ml of toluene were added and the mixture was evaporated. A further 80 ml of toluene were then added and the mixture was left to crystallize. Recrystallization from toluene yielded 15 g of α(S)-(2-benzyloxycarbonylethyl)-1,3-dihydro-1,3-dioxo-2-isoindoleacetic acid of melting point 96°-98° C.; [α]D20 =-50.4° (c=1 in methanol).

Workup

  1. temperatureat reflux temperature for 2 hours
  2. customthe mixture was evaporated
  3. additionA further 80 ml of toluene were then added
  4. waitthe mixture was left
  5. customto crystallize
  6. customRecrystallization from toluene

Sources & evidence

ORD record
ord-53de2e23dd3245e084f4c8875811a97d
Source dataset
uspto-grants-1988_09
Patent number
US04772701

Linked notes

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