Hydrochloric Acid → HCID 178518396, compound

HRID 1668816Notes

Reaction equation

HRID 1668816 reaction equation
Cl[Si](C)(C)C.CO[C:8]([CH:10]1[CH2:14][CH2:13][CH2:12][C:11]1=O)=[O:9].[NH2:16][C:17]([NH2:19])=[O:18].[OH-].[Na+].Cl>CN(C=O)C.O>[N:16]1[C:11]2[CH2:12][CH2:13][CH2:14][C:10]=2[C:8]([OH:9])=[N:19][C:17]=1[OH:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1176UreaHCID 6397ChlorotrimethylsilaneHCID 14798Sodium HydroxideHCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl ester

Product 1

HCID 178518396HCID 178518396, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Chlorotrimethylsilane (20.9 g, 193.6 mmol) was added drop wise under nitrogen to a solution of 2-oxo-cyclopentanecarboxylic acid methyl ester (25 g, 176 mmol) and urea (19.01 g, 316 mmol) in anhydrous DMF (200 mL) at 0° C. After addition, the mixture was warmed to a temperature in the range of 15° C. to 40° C. and stirred for 48 hours. Water was added to the mixture and the resultant precipitate was filtered, washed with water followed by petroleum ether and dried in vacuo. The solid was suspended to a solution of sodium hydroxide (19.9 g, 499 mmol) in water (280 mL) and stirred at 70° C. for 1 hour. After cooling to a temperature in the range of 15° C. to 40° C., concentrated hydrochloric acid was added drop wise to adjust the pH to ˜2. The resultant precipitate was filtered, washed with water and dried in vacuo to afford the title compound as a white solid (21.2 g, 79% yield).

Workup

  1. additionAfter addition
  2. temperaturethe mixture was warmed to a temperature in the range of 15° C. to 40° C.
  3. filtrationthe resultant precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo
  6. stirringstirred at 70° C. for 1 hour
  7. additionwas added drop wise
  8. filtrationThe resultant precipitate was filtered
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-4c6cba1b61e64bba8b5d8d5d01a1ffe1
Source dataset
uspto-grants-2011_08
Patent number
US07989463B2

Reaction notes

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