Hydrochloric Acid → tert-butyl N-(3-{[(tert-butoxy)carbonyl](methyl)amino}-2-hydroxypropyl)-N-methylcarbamate

HRID 604861Notes

Reaction equation

HRID 604861 reaction equation
[Si]([O:8][CH:9]([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])(C(C)(C)C)(C)C.Cl.C([O-])(O)=O.[Na+]>CO>[OH:8][CH:9]([CH2:20][N:21]([CH3:29])[C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57683621HCID 57683621, compound

Product 1

HCID 22485464tert-butyl N-(3-{[(tert-butoxy)carbonyl](methyl)amino}-2-hydroxypropyl)-N-methylcarbamateYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Di-tert-butyl 2-(tert-butyldimethylsilyloxy)propane-1,3-diylbis (methylcarbamate) (21 g, 48.6 mmol) was dissolved into 200 ml methanol at 0° C. Concentrated HCl (4 mL) was added dropwise and the reaction mixture was stirred at RT for 6 hrs. The mixture was placed over an ice water bath and 10 g of NaHCO3 was added slowly. Then the reaction mixture was dried with MgSO4, and then filtered. The filtrate was concentrated to yield 15.0 g of di-tert-butyl 2-hydroxypropane-1,3-diylbis(methylcarbamate) (97%).

Workup

  1. customThe mixture was placed over an ice water bath
  2. dry with materialThen the reaction mixture was dried with MgSO4
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-64bd022e478142a586ba96c767b73516
Source dataset
uspto-grants-2011_03
Patent number
US07910743B2

Reaction notes

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