N-Hydroxyphthalimide → HCID 22722541, compound

HRID 1977966Notes

Reaction equation

HRID 1977966 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([O:25][C:26]1[CH:27]=[C:28]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[O:29][CH2:30][CH2:31][CH2:32][OH:33])(=[O:24])=[O:23])([O-:15])=[O:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[N:58]1[C:62](=[O:63])[C:61]2=[CH:64][CH:65]=[CH:66][CH:67]=[C:60]2[C:59]1=[O:68]>O1CCCC1>[N+:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([O:25][C:26]1[CH:27]=[C:28]([CH:34]=[C:35]([CH3:37])[CH:36]=1)[O:29][CH2:30][CH2:31][CH2:32][O:33][N:58]1[C:59](=[O:68])[C:60]2=[CH:67][CH:66]=[CH:65][CH:64]=[C:61]2[C:62]1=[O:63])(=[O:24])=[O:23])([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22722411HCID 22722411, compound

Product 1

HCID 22722541HCID 22722541, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl azodicarboxylate (910 μL, 5.78 mmol) was slowly added to a solution of 3-[3-(2-nitrophenylsulfonyloxy)-5-methylphenoxy]propanol (1.77 g, 4.82 mmol), as prepared in the preceding step, triphenylphosphine (1.52 g, 5.80 mmol), and N-hydroxyphthalimide (864 mg, 530 mmol) in tetrahydrofuran (10 mL) at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the product purified by flash chromatography (dichloromethane) to give 2.33 g (95%) of the title compound as an oil. 1H-NMR (300 MHz, CDCl3) δ7.98 (dd, 1H, J=7, 1 Hz), 7.67-7.88 (m, 7H), 6.67 (s, 1H), 6.64 (m, 1H), 6.55 (t, 1H, J=2 Hz), 4.36 (t, 2H, J=6 Hz), 4.12 (t, 2H, J=6 Hz), 2.28 (s, 3H), 2.18 (pentet, 2H, J=6 Hz). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid) calcd. for C24H20N2O9S: 535.1 (M+Na). Found 535.0.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe product purified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-d574cf4c71a14d59915abfd332e42e12
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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