Sodium Bicarbonate → (+/-)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-methoxy-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl ester

HRID 1890411Notes

Reaction equation

HRID 1890411 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])[C:10](=[O:24])[NH:9][CH2:8][CH2:7]1)=[O:5])[CH3:2].F[B-](F)(F)F.[CH3:30][O+](C)C.C(=O)([O-])O.[Na+]>ClCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:12][CH:11]([N:13]2[C:14](=[O:23])[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]2=[O:22])[C:10]([O:24][CH3:30])=[N:9][CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 68735785(+/-)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-oxo-[1,4]diazepane-1-carboxylic acid ethyl ester

Product 1

HCID 68736156(+/-)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-5-methoxy-2,3,6,7-tetrahydro-[1,4]diazepine-1-carboxylic acid ethyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 45.00 g (135.82 mmol) of (+/−)-6-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-5-oxo-[1,4]diazepane-1-carboxylic acid ethyl ester in 339 mL of anhydrous dichloromethane was added 22.09 g (149.40 mmol) of trimethyloxonium tetrafluoroborate. The resulting mixture was stirred at room temperature for 12 h. The mixture was hydrolyzed with a saturated aqueous solution of sodium hydrogen carbonate, extracted with dichloromethane, dried over sodium sulfate and the solvent was evaporated to afford 46.90 g (99%) of pure product as yellow oil. The compound was used as such in the next step.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7b9eb44cc65d4b6c9468e173e798ba84
Source dataset
uspto-grants-2013_08
Patent number
US08507476B2

Reaction notes

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