Hydrochloric Acid → N-Carbobenzoxysarcosine

HRID 1896890Notes

Reaction equation

HRID 1896890 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][C:13]([O:15]CC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[Li+].[OH-].Cl>CO>[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 58562640Ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate

Product 1

HCID 97053N-Carbobenzoxysarcosine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl 2-(((benzyloxy)carbonyl)(methyl)amino)acetate (2.66 mg, 10.6 mmol, prepared the previous step) in MeOH (24 mL) and THF (5 mL) and treated with a solution of LiOH (12 mL, 54 mmol, 4.52 M in water). After stirring at room temperature for 3 hours, the pH was adjusted to ˜5 by the addition of aqueous HCl. After extraction with ethyl acetate, the organic layer was dried over Na2SO4 and concentrated in vacuo to yield the product.

Workup

  1. extractionAfter extraction with ethyl acetate
  2. dry with materialthe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto yield the product

Sources & evidence

ORD record
ord-b5cc665c12fd49f0a7f5584f6921bb96
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

Loading…