Sulfuric Acid → HCID 59404602, compound

HRID 58326Notes

Reaction equation

HRID 58326 reaction equation
[C:1]([O:5][C:6]([NH:8]/[C:9](=[N:18]\[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])/[N:10]([CH3:17])[CH2:11][C:12]([O:14]CC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].S(=O)(=O)(O)O>O1CCCC1.C(Cl)Cl>[C:22]([O:21][C:19]([NH:18]/[C:9](=[N:8]\[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])/[N:10]([CH3:17])[CH2:11][C:12]([OH:14])=[O:13])=[O:20])([CH3:24])([CH3:25])[CH3:23]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 59404605HCID 59404605, compound

Product 1

HCID 59404602HCID 59404602, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl N—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N-methylglycinate (630 mg, 1.75 mmol) was dissolved in tetrahydrofuran (6.3 mL) at room temperature. To this was added 1.0 M aqueous sodium hydroxide (0.75 mL, 1.75 mmol). The mixture was stirred at room temperature for 1 hour and then concentrated under vacuum to remove the tetrahydrofuran. The mixture was cooled in an ice bath and acidified with 1 M aqueous sulfuric acid (1.72 mL, 1.75 mmol). The mixture was diluted with methylene chloride, and then the water was removed using anhydrous magnesium sulfate. After filtering, the methylene chloride was removed under vacuum to give the title compound in a quantitative yield.

Workup

  1. concentrationconcentrated under vacuum
  2. customto remove the tetrahydrofuran
  3. temperatureThe mixture was cooled in an ice bath
  4. customthe water was removed
  5. filtrationAfter filtering
  6. customthe methylene chloride was removed under vacuum

Sources & evidence

ORD record
ord-c56e96f6cd8d4f5f8c5a30174eef19db
Source dataset
uspto-grants-2016_09
Patent number
US09434753B2

Reaction notes

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