Hydrochloric Acid → HCID 19930842, compound

HRID 5411Notes

Reaction equation

HRID 5411 reaction equation
[O:1]=[C:2]1[CH:15]([C:16]([O:18]CC)=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:21]([O:23]CC)=[O:22])[NH:3]1.[OH-].[Na+].Cl>C(O)C>[O:1]=[C:2]1[CH:15]([C:16]([OH:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH:4]([C:21]([OH:23])=[O:22])[NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19930817Diethyl 2-oxo-1-azacyclotetradecane-3,14-dicarboxylate

Product 1

HCID 19930842HCID 19930842, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 2-oxo-1-azacyclotetradecane-3,14-dicarboxylate (1.14 g, 3.2 mmol; mixture of both diastereomers) is dissolved in ethanol (32.0 mL). Sodium hydroxide (9.6 mL of a 1N aqueous solution, 9.6 mmol) is added dropwise, and the solution is stirred at room temperature for 3 hours. The reaction is then acidified to pH 3 with 1N hydrochloric acid, and partitioned between ethyl acetate and water. The aqueous phase is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give both diastereomers of 2-oxo-1-azacyclotetradecane-3,14-dicarboxylic acid.

Workup

  1. additionmixture of both diastereomers)
  2. custompartitioned between ethyl acetate and water
  3. extractionThe aqueous phase is extracted several times with ethyl acetate
  4. dry with materialthe combined organic layers are dried (Na2SO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-951c6a1597cb49a28e3182feddd4d406
Source dataset
uspto-grants-1993_09
Patent number
US05244889

Reaction notes

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