Potassium Carbonate → HCID 20482710, compound

HRID 1389369Notes

Reaction equation

HRID 1389369 reaction equation
[OH-].[Na+].[C:3]1([NH:9][CH:10]([CH:16]([OH:18])[CH3:17])[C:11]([O:13]CC)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.O(C1C=C(C=CC=1)CBr)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(P(N(C)C)(N(C)C)=O)C.CCOCC.O.O.CO>[C:3]1([NH:9][CH:10]([CH:16]([OH:18])[CH3:17])[C:11]([OH:13])=[O:12])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 945441-(Bromomethyl)-3-phenoxybenzeneHCID 20482846HCID 20482846, compound

Product 1

HCID 20482710HCID 20482710, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 12679HexamethylphosphoramideSolventHCID 21584184Diethylether waterSolvent

Procedure

To a mixture of ethyl 2-bromo-3-hydroxybutanoate (10 g) and 15 ml of HMPT is added 13.2 g of aniline. The reaction is stirred at RT for 3 days and then taken up in ether followed by washing with dilute sulfuric acid, pH 3, and water. The ether phase is dried over magnesium sulfate and evaporated to yield ethyl 2-phenylamino-3-hydroxybutanoate, which is saponified using 1.6 g of sodium hydroxide, 40 ml of methanol and 20 ml of water with stirring overnight at RT. The acid 2-phenylamino-3-hydroxybutanoic acid (3.0 g) is reacted with m-phenoxybenzyl bromide (3.4 g) in HMPT (20 ml) and potassium carbonate (2.12 g) at 35° for a few hours and worked up using ether/water to yield the m-phenoxybenzyl ester of 2-phenylamino-3-hydroxybutanoic acid.

Sources & evidence

ORD record
ord-fa56c0407b454951a9916ce02d318a84
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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