Hydrogen Bromide → HCID 89924194, compound

HRID 1505685Notes

Reaction equation

HRID 1505685 reaction equation
Br.C(O[C:7]([NH:9][NH:10][CH:11]1[CH2:21][CH2:20][C:14]2([NH:18][C:17](=[O:19])[CH2:16][CH2:15]2)[CH2:13][CH2:12]1)=O)(C)(C)C.[Br:22][CH:23](C=O)[CH:24]=O.[OH-].[Na+]>O.CC(O)=O>[Br:22][C:23]1[CH:7]=[N:9][N:10]([CH:11]2[CH2:12][CH2:13][C:14]3([NH:18][C:17](=[O:19])[CH2:16][CH2:15]3)[CH2:20][CH2:21]2)[CH:24]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 749452-BromopropanedialHCID 89924517HCID 89924517, compound

Product 1

HCID 89924194HCID 89924194, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Hydrobromic acid (1.04 mL of a 48 wt % solution in water; 9.18 mmol; 2.0 eq.) was added to a solution of N′-(2-Oxo-1-aza-spiro[4.5]dec-8-yl)-hydrazinecarboxylic acid tert-butyl ester (1.30 g; 4.59 mmol; 1.0 eq.) and 2-Bromo-malonaldehyde (865 mg; 5.51 mmol; 1.2 eq.) in AcOH (13 mL). The reaction mixture was stirred at RT for 2 hour. It was then basified to pH 5 by addition of a 5N NaOH solution and extracted with DCM (three times). Combined organic phases were washed with brine, dried over magnesium sulfate, filtered and concentrated. Purification by autopreparative LC/MS afforded the title compound as the pure cis-isomer (1.0 g, 94%).

Workup

  1. extractionextracted with DCM (three times)
  2. washCombined organic phases were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by autopreparative LC/MS

Sources & evidence

ORD record
ord-23bd7c4bf11c4342a6e74c5d8aad246e
Source dataset
uspto-grants-2015_12
Patent number
US09216991B2

Reaction notes

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