N-Hydroxyphthalimide → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propionic acid benzyl ester

HRID 732860Notes

Reaction equation

HRID 732860 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[CH:10]([OH:18])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:21]1[C:25](=[O:26])[C:24]2=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]2[C:22]1=[O:31].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:19])[CH:10]([O:18][N:21]1[C:25](=[O:26])[C:24]2[C:23](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]1=[O:31])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 4292412HCID 4292412, compound

Product 1

HCID 689612812-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propionic acid benzyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a mixture of compound from Step 6a (7.00 g, 27.2 mmol), N-hydroxyphthalimide (5.35 g, 32.80 mmol) and PPh3 (9.26 g, 35.30 mmol) in CH2Cl2 (55 mL) was added diisopropyl azodicarboxylate (6.86 mL, 35.38 mmol) during 10 minutes period at −20° C. The resulting mixture was stirred at −20° C. for 2 hours. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, CH2Cl2/hexane=1/2) to afford 10.65 g (99%) of the title compound.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was purified by flash chromatography (silica gel, CH2Cl2/hexane=1/2)

Sources & evidence

ORD record
ord-4b43ca89958a4c08b3cf901a9d70df6e
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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