Triethylamine → HCID 18992017, compound

HRID 375765Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[C:12]1[CH:13]=[C:14]([OH:32])[C:15]([CH3:31])=[C:16]([CH:30]=1)[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18].[C:33]([Si:37]([CH3:40])([CH3:39])Cl)([CH3:36])([CH3:35])[CH3:34].C(N(CC)CC)C>CN(C)C=O>[Si:37]([O:32][C:14]1[C:15]([CH3:31])=[C:16]([CH:30]=[C:12]([N:3]2[C:2](=[O:1])[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4]2=[O:11])[CH:13]=1)[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1)=[O:18])([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:40])[CH3:39]

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 1.0 g of p-nitrobenzyl 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-hydroxy-2-methylbenzoate in 30 ml of dimethylformamide were added 0.71 g of tert-butyldimethylchlorosilane and 0.48 g of triethylamine, and the mixture was stirred at 20° C. for 24 hours. The solvent was evaporated in vacuo, and the residue was partitioned between 2N hydrochloric acid and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was chromatographed on silica gel using methylene chloride as eluent to yield 0.90 g of p-nitrobenzyl 3-(tert-butyldimethylsilyloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl )-2-methylbenzoate as white solid, m.p. 125°-127° C.

Workup

customThe solvent was evaporated in vacuo
customthe residue was partitioned between 2N hydrochloric acid and ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
customthe solvent was evaporated in vacuo
customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record: ord-ebb8249fb1414671ae8c265202e66315
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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