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

HRID 1529609Notes

Reaction equation

HRID 1529609 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) δ7.17 (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-c65fc1cecd4041f58bf3d8eff90d4fe0
Source dataset
uspto-grants-2015_07
Patent number
US09090619B2

Reaction notes

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