Potassium Hydroxide → HCID 59367167, compound

HRID 1923982Notes

Reaction equation

HRID 1923982 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]([N:22]=O)[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[K+]>CO.O.[Cl-].[Ti+3].[Cl-].[Cl-]>[C:17]([O:16][C:15]([NH:14][CH2:13][CH2:12][N:11]([CH2:10][CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[NH2:22])=[O:21])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 14797Potassium HydroxideHCID 59366932HCID 59366932, compound

Product 1

HCID 59367167HCID 59367167, compound

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of tert-butyl N-{2-[(2-{[(tert-butoxy)carbonyl]amino}ethyl)(nitroso)amino]ethyl}carbamate LIV (2 g; 6.02 mmol) in methanol (15 mL) was added a solution of titanium (III) chloride (3.7 g; 24.07 mmol) in water (20 mL). The mixture was stirred for 1.5 h and then cooled in a ice/water bath before adding KOH (12 g) in portions for 40 min. Stirring was continued for an additional 1 h at r.t. The reaction was filtered, solvent evaporated and purified on a silica gel column (1:1 chloroform/methanol) to obtain crude tert-butyl N-{2-[1-(2-{[(tert-butoxy)carbonyl]amino}ethyl)hydrazin-1-yl]ethyl}carbamate LV (0.85 g) used directly for step 5. ESIMS found for C15H32N3O4 m/z 319.4 (M+H).

Workup

  1. temperaturecooled in a ice/water bath
  2. stirringStirring
  3. waitwas continued for an additional 1 h at r.t
  4. filtrationThe reaction was filtered
  5. customsolvent evaporated
  6. custompurified on a silica gel column (1:1 chloroform/methanol)

Sources & evidence

ORD record
ord-89d946996ccc4962b09d339dba14a86e
Source dataset
uspto-grants-2012_05
Patent number
US08178490B2

Reaction notes

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