N-Hydroxyphthalimide → HCID 68960737, compound

HRID 732856Notes

Reaction equation

HRID 732856 reaction equation
[CH2:1]([O:8][C:9](=[O:18])[CH:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:18])[CH:10]([O:17][N:20]1[C:24](=[O:25])[C:23]2[C:22](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]1=[O:30])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 13461alpha-Hydroxybenzeneacetic acid phenylmethyl esterHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 68960737HCID 68960737, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of benzyl-2-hydroxy-2-phenylacetate (2.42 g, 10 mmol), N-hydroxyphthalimide (1.96 g, 12 mmol) and PPh3 (3.4 g, 13 mmol) in CH2Cl2 (30 mL) was added DIAD (2.63 g, 13 mmol) at −20° C. The resulting mixture was stirred at −20° C. for 1 hour. The reaction mixture was concentrated and purified by flash chromatography (silica gel, Hexanes/CH2Cl2=1/3) giving 3.8 g (98%) of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by flash chromatography (silica gel, Hexanes/CH2Cl2=1/3)

Sources & evidence

ORD record
ord-903c4f365544407aaef4b4c6066cb3bf
Source dataset
uspto-grants-2009_09
Patent number
US07589067B2

Reaction notes

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