Citric Acid → HCID 12531280, compound

HRID 1186386Notes

Reaction equation

HRID 1186386 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:5])=O.C[Si](Cl)(C)C.C(Cl)(=O)C(Cl)=O.[CH2:23]([NH2:25])[CH3:24].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>ClCCl.CN(C1C=CN=CC=1)C.CO.N1C=CC=CC=1.O1CCCC1.CN(C)C=O>[CH2:23]([NH:25][C:3](=[O:5])[CH:2]([OH:1])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:24]

Participants

12

Reactant 5

HCID 311Citric AcidHCID 1292Mandelic AcidHCID 6341EthylamineHCID 6397ChlorotrimethylsilaneHCID 65578Oxalyl chloride

Product 1

HCID 12531280HCID 12531280, compoundYield 83%

Reagents, catalysts & solvents 6

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

According to Reference Example 8-56, 2-hydroxy-2-phenylacetic acid (500 mg, 3.29 mmol) was dissolved in dichloromethane (7.5 mL), and the solution was stirred with pyridine (0.532 mL, 6.58 mmol), DMAP (40 mg, 0.33 mmol), trimethylsilyl chloride (0.835 mL, 6.58 mmol), N,N-dimethylformamide (0.050 mL), oxalyl chloride (0.301 mL, 3.45 mmol), a solution containing a 2 mol/L tetrahydrofuran solution of ethylamine (1.81 mL, 3.62 mmol) and pyridine (0.878 mL), and a solution containing a methanol (5 mL) and citric acid (695 mg, 3.62 mmol). Thus, N-ethyl-2-hydroxy-2-phenylacetamide (Compound EF) (489 mg, yield: 83%) was obtained.

Sources & evidence

ORD record
ord-dcdbe5f3da9a46048844b97371fee305
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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