Sodium Hydroxide → HCID 86737024, compound

HRID 1706133Notes

Reaction equation

HRID 1706133 reaction equation
[CH3:1][C:2]1([C:17]([O:19]CC)=[O:18])[N:3]2[CH:6]([O:7]/[C:8]/1=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:4]2=[O:16].[OH-].[Na+:23]>C1COCC1>[CH3:1][C:2]1([C:17]([O-:19])=[O:18])[N:3]2[CH:6]([O:7]/[C:8]/1=[CH:9]\[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][C:4]2=[O:16].[Na+:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86737025HCID 86737025, compound

Product 1

HCID 86737024HCID 86737024, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl (Z)-2-methyl-3-benzylidene-7-oxo-4-oxa-1-azabicyclo[3.2.0]-heptane-2-carboxylate (0.05 g, 0.174 mmole) was dissolved in 2 ml THF/2 ml H2O, ice cooled and treated with 1 N NaOH (0.174 ml). After 2 hours the solution was ether washed, brought to pH 7 with dil. HCl and freeze dried to yield the title compound (82%) as a off-white solid. νmax (KBr): 1772, 1673, 1600, 1390, 1208, 1034 cm-1. δ(D2O-ref HOD=4.45δ); 1.64 (s, 3H, 2-CH3), 2.88 (d, J=17 Hz, 1H, C6-H trans to C5-H), 3.30 (dd, J=17 and 2.5 Hz, 1H, C6-H cis to C5-H), 5.40 (s, 1H, =CH-), 5.58 (d, J=2.5 Hz, 1H, C5-H), 7.0-7.6 (m, 5H, Ph). λmax (EtOH): 270 nm (ε=18380).

Workup

  1. temperatureice cooled
  2. washether washed
  3. customdried

Sources & evidence

ORD record
ord-0401f749460f4a318a9f9a8781580bdd
Source dataset
uspto-grants-1980_06
Patent number
US04206120

Reaction notes

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