Hydrochloric Acid → HCID 86679446, compound

HRID 1776498Notes

Reaction equation

HRID 1776498 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[CH2:9][C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH3:25])[CH:17]=1)[CH2:9][C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86679445HCID 86679445, compound

Product 1

HCID 86679446HCID 86679446, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-(tert-butoxycarbonyl(3,4-dimethoxybenzyl)amino)-acetate (0.260 g, 0.736 mmol) in THF (1.5 ml), lithium hydroxide 1N (0.883 ml, 0.883 mmol) was added, and the reaction was stirred at RT for 4 hours. The mixture was diluted with EtOAc (15 ml) and acidified with HCl 1M. The organic phase was washed with brine and dried over Na2SO4; the solvent was evaporated to dryness affording 2-(tert-butoxycarbonyl(3,4-dimethoxybenzyl)amino)acetic acid as a yellow oil (0.233 g, 0.716 mmol, 97% yield, MS/ESI+ 348.1 [MNa]+). This product was used without any further purification.

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-0ca86624a3a2422e8b837b6eced80c60
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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