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

HRID 1883092Notes

Reaction equation

HRID 1883092 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-62137b8963454b438f3e9a06fe83d577
Source dataset
uspto-grants-2004_07
Patent number
US06759424B2

Reaction notes

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