Lithium Hydroxide → 2-(2-((tert-Butoxycarbonyl)(methyl)amino)-N-methylacetamido)acetic acid

HRID 401244Notes

Reaction equation

HRID 401244 reaction equation
C([O:3][C:4](=[O:20])[CH2:5][N:6]([C:8](=[O:19])[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:11])[CH3:7])C.[Li+].[OH-]>O.C1COCC1>[C:15]([O:14][C:12]([N:10]([CH3:11])[CH2:9][C:8]([N:6]([CH2:5][C:4]([OH:20])=[O:3])[CH3:7])=[O:19])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57470192{[2-(Tert-butoxycarbonyl-methyl-amino)acetyl]-methyl-amino}-acetic acid ethyl ester

Product 1

HCID 513582342-(2-((tert-Butoxycarbonyl)(methyl)amino)-N-methylacetamido)acetic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid ethyl ester (12.3 g, 42.7 mmol) and LiOH (8.9 g, 214 mmol) in H2O (20 mL) and THF (100 mL) was stirred overnight. Volatile solvent was removed under vacuum and the residue was extracted with ether (2×100 mL). The aqueous phase was acidified to pH 3 with dilute HCl solution, and then extracted with CH2Cl2 (2×300 mL). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated under vacuum to give {[2-(tert-butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid as a colorless oil (10 g, 90%). 1H NMR (CDCl3) δ 7.17 (br s, 1H), 4.14-4.04 (m, 4H), 3.04-2.88 (m, 6H), 1.45-1.41 (m, 9H); ESI-MS 282.9 m/z (M+Na+).

Workup

  1. customVolatile solvent was removed under vacuum
  2. extractionthe residue was extracted with ether (2×100 mL)
  3. extractionextracted with CH2Cl2 (2×300 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3eef61e0aad1439cae8a1edb87b4fb3f
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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