Sodium Hydroxide → 3-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)propanoic acid

HRID 720935

Reaction equation

HRID 720935 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21893946Ethyl 3-(2-{(tert-butoxycarbonyl)amino}acetylamino)propionate

Product 1

HCID 218938843-(2-{[(Tert-butoxy)carbonyl]amino}acetamido)propanoic acidYield 16%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (6) at 0° C. (3.43 g; 0.012 mmol) in methanol (40 ml) was treated with 2N sodium hydroxide (6.9 ml; 0.013 mmol). The mixture was stirred at ambient temperature for 90 minutes. After evaporation of the methanol and removal of the insoluble material by filtration, the solution was adjusted to pH5 with 6N hydrochloric acid. The mixture was extracted with dichloromethane and the organic layer evaporated to dryness to give 3-[(2-tertbutoxycarbonylaminoacetyl)amino]propanoic acid (7).

Workup

  1. customAfter evaporation of the methanol and removal of the insoluble material
  2. filtrationby filtration
  3. extractionThe mixture was extracted with dichloromethane
  4. customthe organic layer evaporated to dryness

Sources & evidence

ORD record
ord-47c9c7199684463cb7fc161e44a736b1
Source dataset
uspto-grants-2006_11
Patent number
US07135502B1

Linked notes

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