Sodium Hydroxide → Ethyl 5-benzyl-2,4-dioxo-3-[(1R)-1-phenylethyl]-1,3-oxazolidine-5-carboxylate

HRID 1526507Notes

Reaction equation

HRID 1526507 reaction equation
[OH-].[Na+].[CH2:3]([C:10]([OH:21])([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:22]([C@@H:25]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH3:26])=[C:23]=[O:24]>C1COCC1>[CH2:3]([C:10]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[O:21][C:23](=[O:24])[N:22]([C@@H:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH3:26])[C:16]1=[O:18])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 7018262(R)-(+)-1-Phenylethyl isocyanateHCID 15828909Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate

Product 1

HCID 89509948Ethyl 5-benzyl-2,4-dioxo-3-[(1R)-1-phenylethyl]-1,3-oxazolidine-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a mixture of NaOH (25 g) and 15.7 g of activated molecular sieves in 1159 mL of THF at 0° C. was added a 1159 mL THF solution of diethyl benzyl(hydroxy)propanedioate (153 g). After 5 min, to this mixture was added [(1R)-1-isocyanatoethyl]benzene (118 g). The mixture was stirred at 0° C. for 30 min and then warmed to ambient temperature and stirred for 4 h. The reaction mixture was directly purified using a Biotage silica gel chromatography system (5-30% ethyl acetate in hexanes) to give the title compound.

Workup

  1. temperaturewarmed to ambient temperature
  2. stirringstirred for 4 h
  3. customThe reaction mixture was directly purified

Sources & evidence

ORD record
ord-9ac5460468194a589599798cca883014
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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