Water → HCID 54066124, compound

HRID 341775Notes

Reaction equation

HRID 341775 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][CH:14]([C:18]([OH:20])=[O:19])C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[Cl-].[Na+].[CH3:24]N(C=O)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]=[C:10]([CH2:13][CH2:14][C:18]([O:20][CH3:24])=[O:19])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 69945705HCID 69945705, compound

Product 1

HCID 54066124HCID 54066124, compoundYield 92%

Conditions

Temperature
150 °C

Procedure

To a solution of 4.52 g (14.4 mmol) 2-(1-tert.-butoxycarbonyl-2,5-dihydro-1H-pyrrol-3-yl-methyl)-malonic acid idimethylester n 140 ml DMF were added 1.94 g (108 mmol) water and 1.26 g( 21.6 mmol) sodium chloride. The mixture was degassed and heated to 150° C. for 30 h under an atmosphere of argon. After this period of time no starting material could be detected by TLC. The mixture was cooled to room temperature, diluted with 200 ml ether and washed three times with water, then with brine. The organic layer was dried over MgSO4 and evaporated. Purification by bulb-to-bulb distillation gave 3.38 g (92%) of 3-(2-methoxycarbonyl-ethyl)-2,5-dihydropyrrole-1-carboxylic acid tert. butylester as a colorless oil, b.p. 130° C. (0.2 mbar).

Workup

  1. customThe mixture was degassed
  2. waitAfter this period of time no starting material could be detected by TLC
  3. temperatureThe mixture was cooled to room temperature
  4. additiondiluted with 200 ml ether
  5. washwashed three times with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customPurification
  9. distillationby bulb-to-bulb distillation

Sources & evidence

ORD record
ord-1a6bd0a0643742568286b72310b3c31a
Source dataset
uspto-grants-1999_01
Patent number
US05856309

Reaction notes

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