Ethyl bromoacetate → HCID 20031089, compound

HRID 232158Notes

Reaction equation

HRID 232158 reaction equation
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11](CO)=[N:10]2)=[CH:5][CH:4]=1.BrCC(OCC)=O.C([O:29][C:30](=[O:34])[CH2:31][O:32][CH3:33])C.[OH-].[Na+]>C1COCC1.C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:11]([CH:31]([O:32][CH3:33])[C:30]([OH:29])=[O:34])=[N:10]2)=[CH:7][CH:8]=1

Participants

8

Reactant 5

HCID 7748Ethyl bromoacetateHCID 14798Sodium HydroxideHCID 77544Ethyl 2-methoxyacetateHCID 5360545SodiumHCID 14576224HCID 14576224, compound

Product 1

HCID 20031089HCID 20031089, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of sodium hyride (0.63 g) in THF (65 ml) was treated with the compound of Example 77 (4.0 g) and heated at 60° C. for 3 hours. Ethyl bromoacetate (10.9 g) was added to the cooled mixture and the reaction was allowed to proceed at ambient temperature overnight. The crude methoxy acetic acid ethyl ester was poured into ethanol (200 ml), treated with 3N sodium hydroxide and heated at reflux temperature for 1.5 hours. The solution was concentrated to 100 ml, diluted to 250 ml with water and unreacted compound of Example 77 extracted into ethyl acetate. The aqueous phase was acidified and crude product filtered. Ethanol crystallization gave the title compound (2.18 g, m.p. 123° C.). An analytical sample, m.p. 183° C., was obtained from ethanol solution.

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 1.5 hours
  3. concentrationThe solution was concentrated to 100 ml
  4. additiondiluted to 250 ml with water and unreacted compound of Example 77
  5. extractionextracted into ethyl acetate
  6. filtrationcrude product filtered
  7. customEthanol crystallization

Sources & evidence

ORD record
ord-e3ba318856ff43acb0ab9b5de7199caf
Source dataset
uspto-grants-1989_07
Patent number
US04851425

Reaction notes

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