Phthalimide → HCID 89666923, compound

HRID 2171267Notes

Reaction equation

HRID 2171267 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.O[CH:46]([CH:57]([CH3:59])[CH3:58])[C@@H:47]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[CH3:48]>C1COCC1>[O:6]=[C:4]1[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1](=[O:11])[N:5]1[C@H:46]([CH:57]([CH3:59])[CH3:58])[C@@H:47]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:54])([CH3:53])[CH3:55])[CH3:48]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89666915HCID 89666915, compound

Product 1

HCID 89666923HCID 89666923, compoundYield 35.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Phthalimide (4.3 g), triphenylphosphine (9.6 g), and DIAD (19.2 ml) were added to a THF (40 ml) solution containing tert-butyl ((2S)-3-hydroxy-4-methylpentan-2-yl)carbamate (5.3 g) obtained in the 4th step, followed by stirring at room temperature for 16 hours. The solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 5:1). Yellow oily matter of tert-butyl ((2S,3R)-3-(1,3-dioxoisoindolin-2-yl)-4-methylpentan-2-yl)carbamate (3 g) was thus obtained.

Workup

  1. customobtained in the 4th step
  2. distillationThe solvent was distilled away under reduced pressure
  3. customthe obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=1:0 to 5:1)

Sources & evidence

ORD record
ord-d517ccf25c4d48c2911c19bed570fac3
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

Loading…