Hydrochloric Acid → HCID 14551016, compound

HRID 249400Notes

Reaction equation

HRID 249400 reaction equation
C[C:2]([OH:13])([C:9]([O:11][CH3:12])=[O:10])C1C=CC=CC=1.[C:14](Cl)(Cl)=[O:15].[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.Cl.[C:25]1([CH3:31])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C)C=O.CCOCC.CCCCCC.C(Cl)Cl>[CH3:12][O:11][C:9](=[O:10])[C@@H:2]([O:13][C:14]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:15])[CH2:31][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 6371PhosgeneHCID 8083MorpholineHCID 578110(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester

Product 1

HCID 14551016HCID 14551016, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolventHCID 21584099Diethylether hexaneSolvent

Procedure

To L-phenyllactic acid methyl ester (3.2 g) was added 150 mL of 12.5% phosgene in toluene and 25 drops of dimethylformamide. After stirring for 16 h at room temperature, the solvent was evaporated and the residue chased several times with benzene. The resulting product was dissolved in methylene chloride (50 mL), cooled to 0° C. and treated by dropwise addition with 3.86 g (0.044 mol) of morpholine. The reaction mixture was stirred for 2 h at 0°-5° C. and then distributed between 0.5N HCl and methylene chloride. The organic phase was washed with aqueous NaHCO3 and brine and evaporated to a residue. Flash chromatography on silica gel eluting with 2/1 ether hexane gave a 65% yield of product. NMR (300 MHz): 3.08 (dd, 1H), 3.20 (dd, 1H), 3.8 (s, 3H), 5.19 (dd, 1H).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe resulting product was dissolved in methylene chloride (50 mL)
  3. temperaturecooled to 0° C.
  4. stirringThe reaction mixture was stirred for 2 h at 0°-5° C.
  5. washThe organic phase was washed with aqueous NaHCO3 and brine
  6. customevaporated to a residue

Sources & evidence

ORD record
ord-d86d87619382429787f4dff0162b8b6e
Source dataset
uspto-grants-1993_05
Patent number
US05214129

Reaction notes

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