Hydrochloric Acid → HCID 11761871, compound

HRID 977232Notes

Reaction equation

HRID 977232 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)=[O:16].C(O)C.[BH4-].[Na+].Cl>O1CCCC1.O>[OH:16][CH:15]([C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][CH:26]2[O:30][C:29](=[O:31])[NH:28][C:27]2=[O:32])=[CH:19][CH:18]=1)[CH2:14][CH2:13][C:3]1[N:4]=[C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:6][C:2]=1[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 10961013HCID 10961013, compound

Product 1

HCID 11761871HCID 11761871, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[3-[4-[3-(5-methyl-2-phenyl-4-oxazolyl)propionyl]phenyl]propyl]-2,4-oxazolidinedione (0.25 g) in tetrahydrofuran (THF) (10 ml)-ethanol (10 ml), sodium borohydride (0.05 g) was added, followed by stirring at room temperature for 2 hours. The reaction mixture was poured over water, neutralized with 2N HCl and then extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and then concentrated under reduced pressure; the residue was purified by silica gel column chromatography. From the fraction eluted with ethyl acetate-chloroform (1:1), 5-[3-[4 -[1-hydroxy-3-(5-methyl-2-phenyl-4oxazoly) propyl]phenyl]propyl]-2,4-oxazolidinedione (0.16 g, 64%) was obtained, which was then recrystallized from acetone-isopropyl ether to yield colorless needles having a melting point of 150°-151° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. washFrom the fraction eluted with ethyl acetate-chloroform (1:1)

Sources & evidence

ORD record
ord-b077139f103548de9b7dc6260c5593fd
Source dataset
uspto-grants-1997_03
Patent number
US05614544

Reaction notes

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