Ethanol → Ethyl 3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxo-4-imidazolidineheptanoate

HRID 444051Notes

Reaction equation

HRID 444051 reaction equation
[C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:14]([CH2:15][CH2:16][CH:17]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[OH:18])[C:13](=[O:25])[NH:12][C:11]1=[O:26])([OH:3])=[O:2].[CH2:27](O)[CH3:28]>S(=O)(=O)(O)O>[CH2:27]([O:2][C:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH:10]1[N:14]([CH2:15][CH2:16][CH:17]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]2)[OH:18])[C:13](=[O:25])[NH:12][C:11]1=[O:26])=[O:3])[CH3:28]

Participants

4

Reactant 2

HCID 702EthanolHCID 1193043-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxoimidazolidine-4-heptanoic acid

Product 1

HCID 12788653Ethyl 3-(3-cyclohexyl-3-hydroxypropyl)-2,5-dioxo-4-imidazolidineheptanoate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-(6-carboxyhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin (diastereomer of m.p. 96°-98°) (Example 14c) (4 g) in ethanol (60 ml) and concentrated sulphuric acid (1.6 ml) was allowed to stand at room temperature for 18 hours. The alcohol was evaporated, water was added, and the precipitated oil was extracted with ether. The ether solution was washed with sodium bicarbonate solution and with water, dried (MgSO4) and evaporated to give a single diastereomer of 5-(6-ethoxycarbonylhexyl)-1-(3-cyclohexyl-3-hydroxypropyl)hydantoin as a colourless oil, soon solidifying, and crystallising from cyclohexane in small colourless plates, m.p. 62°-63°.

Workup

  1. customThe alcohol was evaporated
  2. additionwater was added
  3. extractionthe precipitated oil was extracted with ether
  4. washThe ether solution was washed with sodium bicarbonate solution and with water
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-aabcae5ebaad4079ab40c8dc76385edb
Source dataset
uspto-grants-1981_04
Patent number
US04262128

Reaction notes

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