Hydrochloric Acid → HCID 53696547, compound

HRID 362447Notes

Reaction equation

HRID 362447 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:14]([O:26][Si](C)(C)C)[CH2:15][N:16]([CH2:20][CH:21](OC)OC)[C:17]([NH2:19])=[O:18])[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1.Cl>CO>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:14]([OH:26])[CH2:15][N:16]3[CH:20]=[CH:21][NH:19][C:17]3=[O:18])[CH:9]=[CH:10][C:11]=2[O:12][CH3:13])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69685943HCID 69685943, compound

Product 1

HCID 53696547HCID 53696547, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (±)-N-[2-[3-(cyclopropylmethoxy)-4-methoxyphenyl]-2-[(trimethylsilyl)-oxy]ethyl]-N-(dimethoxyethyl)urea (39.6 g) and HCl (150 ml) in methanol (450 ml) was stirred for 48 hours at RT. The resulting mixture was concentrated and the concentrate (150 ml) was extracted three times with CH2Cl2. The combined organic layer were poured out into a NaOH solution. The mixture was stirred and the layers were separated. The aqueous phase was extracted twice with CH2Cl2. The separated organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from ethylacetate/diisopropyl ether. The precipitate was filtered off and dried, yielding 10.36 g (37.9%) of 1-[2-[3-(cyclopropylmethyloxy)-4-methoxyphenyl]-2-hydroxy-ethyl]-1,3-dihydro-2H-imidazol-2-one (interm. 6).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. concentrationthe concentrate (150 ml)
  3. extractionwas extracted three times with CH2Cl2
  4. additionThe combined organic layer were poured out into a NaOH solution
  5. stirringThe mixture was stirred
  6. customthe layers were separated
  7. extractionThe aqueous phase was extracted twice with CH2Cl2
  8. dry with materialThe separated organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent was evaporated
  11. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 95/5)
  12. customThe pure fractions were collected
  13. customthe solvent was evaporated
  14. customThe residue was crystallized from ethylacetate/diisopropyl ether
  15. filtrationThe precipitate was filtered off
  16. customdried

Sources & evidence

ORD record
ord-f1e459cbd25043ca9e20c48e7046eb30
Source dataset
uspto-grants-1999_02
Patent number
US05869515

Reaction notes

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