Hydrazine → HCID 10683057, compound

HRID 1845356Notes

Reaction equation

HRID 1845356 reaction equation
NN.CC([CH2:7][N:8]([CH2:12][CH2:13][CH:14]([N:21]1C(=O)C2C(=CC=CC=2)C1=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9](=[O:11])[O-:10])(C)C>C1COCC1.CO>[NH2:21][CH:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH2:13][CH2:12][N:8]([CH3:7])[C:9](=[O:11])[O:10][C:15]([CH3:20])([CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 86633540HCID 86633540, compound

Product 1

HCID 10683057HCID 10683057, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

NH2NH2 (1.7 mL, 54.2 mmol) was added to a THF/MeOH (50 mL/10 mL) solution of 1,1-dimethylethyl[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl]methylcarbamate (2.7 g, 6.8 mmol) and stirred overnight. After 12 hours, the solution was absorbed onto silica and purified by column chromatography using 5% MeOH in CHCl3 containing 0.5% NH4OH to give the title compound (1.4 mg, 77%) as a white solid: LC-MS (ES) m/z=265 (M+H)+.

Workup

  1. waitAfter 12 hours
  2. customthe solution was absorbed onto silica
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-671538ae3ae442a49419f47866bd4b83
Source dataset
uspto-grants-2015_02
Patent number
US08946278B2

Reaction notes

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