N-Hydroxyphthalimide → HCID 22633854, compound

HRID 1369313Notes

Reaction equation

HRID 1369313 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][C:34]1[CH:67]=[CH:66][C:37]([C:38]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64]O)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:39]2[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=2)=[CH:36][CH:35]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:38]([O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:1][N:2]2[C:3](=[O:12])[C:4]3=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]3[C:6]2=[O:7])([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:37]2[CH:36]=[CH:35][C:34]([O:33][CH3:32])=[CH:67][CH:66]=2)=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 10665N-HydroxyphthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22633851HCID 22633851, compound

Product 1

HCID 22633854HCID 22633854, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-hydroxyphthalimide (0.7 g, 4.3 mmol) and triphenylphosphine (1.1 g, 4.2 mmol) were added to a solution of 11-(4,4′-dimethoxytrityloxy)-3,6,9-trioxaundecanol (2.0 g, 4.0 mmol) in THF (60 mL). Diethylazodicarboxylate (DEAD, 0.7 mL, 3.6 mmol) was added dropwise and the stirring was continued overnight at ambient temperature. The reaction mixture was evaporated to an oil, applied onto a silica gel column, and eluted with a linear gradient from neat CH2Cl2 to a 97:3 (v/v) mixture of CH2Cl2 and MeOH. The purification was repeated to yield 2.1 g (80%) of the title compound.

Workup

  1. customThe reaction mixture was evaporated to an oil
  2. washeluted with a linear gradient from neat CH2Cl2 to a 97:3 (v/v) mixture of CH2Cl2 and MeOH
  3. customThe purification

Sources & evidence

ORD record
ord-c94f8a2cf1b5498fb64c628b359b6493
Source dataset
uspto-grants-2003_06
Patent number
US06576752B1

Reaction notes

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