Sodium Hydroxide → 2-((tert-Butoxycarbonyl)amino)malonic acid

HRID 2269810Notes

Reaction equation

HRID 2269810 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:15]([O:17]CC)=[O:16])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][CH:9]([C:10]([OH:12])=[O:11])[C:15]([OH:17])=[O:16])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 382219Diethyl 2-((tert-butoxycarbonyl)amino)malonate

Product 1

HCID 183481032-((tert-Butoxycarbonyl)amino)malonic acidYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine diethyl t-butoxycarbonylaminomalonate (4.55 g, 16.5 mmol), a 6 M aqueous sodium hydroxide solution (6.65 mL, 40 mmol), and ethanol (30 mL). After 18 hours, evaporate in vacuo to remove most of the ethanol, dilute with water (50 mL) and extract with diethyl ether. Acidify to a pH of about 3 with aqueous 12M hydrochloric acid and extract twice with ethyl acetate. Dry the combined organic layers over Na2SO4, filter, and concentrate in vacuo to give the title compound (61%).

Workup

  1. customevaporate in vacuo
  2. customto remove most of the ethanol
  3. additiondilute with water (50 mL)
  4. extractionextract with diethyl ether
  5. extractionextract twice with ethyl acetate
  6. dry with materialDry the combined organic layers over Na2SO4
  7. filtrationfilter
  8. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-f6b00348ff464d4b934e438b52ea0a6c
Source dataset
uspto-grants-2001_12
Patent number
US06329550B1

Reaction notes

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