Water → ((s)-4-(4-Hydroxymethylphenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetic acid

HRID 2230218Notes

Reaction equation

HRID 2230218 reaction equation
O.[BH4-].[Na+].[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([C@@:12]2([CH3:37])[C:16](=[O:17])[N:15]([CH2:18][C:19]([O:21]CC3C=CC=CC=3)=[O:20])[C:14](=[O:29])[N:13]2[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:8][CH:7]=1)=[O:5]>C(O)C>[OH:5][CH2:4][C:6]1[CH:11]=[CH:10][C:9]([C@@:12]2([CH3:37])[C:16](=[O:17])[N:15]([CH2:18][C:19]([OH:21])=[O:20])[C:14](=[O:29])[N:13]2[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86588626Benzyl ((S)-4-(4-formylphenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetate

Product 1

HCID 69027157((s)-4-(4-Hydroxymethylphenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

20 ml of water and then, at 0° C., 22 mg (0.6 mmol) of sodium borohydride were added to a solution of 500 mg (1.1 mmol) of 8.2 in 50 ml of ethanol. After stirring at 0° C. for 40 min, the reaction mixture was concentrated in vacuo, the residue was heated at 50° C. for 12 h in 30 ml of 6 N hydrochloric acid/THF (1:1) and the reaction mixture was allowed to stand overnight at room temperature. The mixture was extracted with dichloromethane and the organic phase was dried over sodium sulfate. After filtration, the solvent was removed in vacuo, and the residue was treated with water and freeze-dried. 440 mg of crude 8.3 were obtained, which was employed in the next synthesis step without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. temperaturethe residue was heated at 50° C. for 12 h in 30 ml of 6 N hydrochloric acid/THF (1:1)
  3. waitto stand overnight at room temperature
  4. extractionThe mixture was extracted with dichloromethane
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was removed in vacuo
  8. additionthe residue was treated with water
  9. customfreeze-dried
  10. custom440 mg of crude 8.3 were obtained
  11. customwhich was employed in the next synthesis step without further purification

Sources & evidence

ORD record
ord-a7e9d0d0607e40fd845961c9756e0dc5
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

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