N-Hydroxyphthalimide → n-[3-[3-(5-Chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimide

HRID 1977936Notes

Reaction equation

HRID 1977936 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:36][CH3:37])=[C:18]([S:20]([O:23][C:24]2[CH:25]=[C:26]([CH:32]=[C:33]([CH3:35])[CH:34]=2)[O:27][CH2:28][CH2:29][CH2:30][OH:31])(=[O:22])=[O:21])[CH:19]=1.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>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([O:36][CH3:37])=[C:18]([S:20]([O:23][C:24]2[CH:25]=[C:26]([CH:32]=[C:33]([CH3:35])[CH:34]=2)[O:27][CH2:28][CH2:29][CH2:30][O:31][N:58]2[C:59](=[O:68])[C:60]3=[CH:67][CH:66]=[CH:65][CH:64]=[C:61]3[C:62]2=[O:63])(=[O:21])=[O:22])[CH:19]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 227224523-[3-(5-Chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propanol

Product 1

HCID 22722408n-[3-[3-(5-Chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propoxy]phthalimideYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Diethyl azodicarboxylate (0.16 mL, 0.95 mmol) was added dropwise over 6 min to 3-[3-(5-chloro-2-methoxyphenylsulfonyloxy)-5-methylphenoxy]propanol (0.31 g, 0.79 mmol, prepared in the preceding step), triphenylphosphine (0.25 g, 0.93 mmol) and N-hydroxyphthalimide (0.13 g, 0.80 mmol) in anhydrous tetrahydrofuran (7.9 mL) at 0° C. under a nitrogen atmosphere. The solution was stirred 0° C. for an adddional 15 min then at ambient temperature overnight. The reaction mixture was concentrated, and the crude product was purified by flash column chromatography (1% acetone in dichloromethane) to give the title compound (0.417 g, 99%) as a colorless foam. 1H-NMR (300 MHz, CDCl3) δ7.88-7.75 (m, 5H), 7.56 (dd, 1H, J=8.9, 2.7 Hz), 7.05 (d, 1H, J=8.9 Hz), 6.64 (br s, 1H), 6.57 (br s, 1H), 6.43 (t, 1H, J=2 Hz), 4.37 (t, 2H, J=6.1 Hz), 4.12 (t, 2H, J=6.2 Hz), 4.03 (s, 3H), 2.28 (s, 3H), 2.19 (pentet, 2H, J=6.1 Hz). Mass spectrum (MALDI-TOF, gentisic acid matrix) calcd. for C25H22ClNO8S: 554.1 (M+Na). Found: 553.7.

Workup

  1. customat ambient temperature
  2. customovernight
  3. concentrationThe reaction mixture was concentrated
  4. customthe crude product was purified by flash column chromatography (1% acetone in dichloromethane)

Sources & evidence

ORD record
ord-2949c796f6204b479a726b4c51f26ffc
Source dataset
uspto-grants-2001_05
Patent number
US06235778B1

Reaction notes

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