Pyridine → HCID 22808522, compound

HRID 1862887Notes

Reaction equation

HRID 1862887 reaction equation
[OH:1][CH2:2]/[CH:3]=[C:4]1/[CH:5]([O:12][CH3:13])[N:6]2[C@H:9]([O:10]/1)[CH2:8][C:7]2=[O:11].[C:14]1([CH2:20][C:21](Cl)=[O:22])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.N1C=CC=CC=1>C(OCC)C.C(OCC)(=O)C>[CH3:13][O:12][CH:5]1[N:6]2[C@H:9]([O:10]/[C:4]/1=[CH:3]\[CH2:2][O:1][C:21](=[O:22])[CH2:20][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:8][C:7]2=[O:11]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 70608580HCID 70608580, compound

Product 1

HCID 22808522HCID 22808522, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

(Z)-(5R)-3-(2-Hydroxyethylidene)-2-methoxy-4-oxa-1-azabicyclo[3.2.0]heptan-7-one (15 mg.) was dissolved in dry diethyl ether (2 ml.) and the solution was stirred and ice-cooled with exclusion of moisture while phenylacetyl chloride (30 mg.) followed by dry pyridine (15 mg.) were added. The mixture was kept at 4° with exclusion of moisture for 15 hours. The mixture was diluted with ethyl acetate (30 ml.) and was washed with 5% sodium chloride solution (10 ml.) and saturated sodium chloride solution (10 ml.). The solution was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to yield a yellow gum. Chromatography of the gum on silica gel (10 g.) using ethyl acetate/petroleum ether (b.p. 60°-80°) gave the title compound as a colourless gum (17 mg.). [α]D22 =+45.6° (c=1.0, CHCl3). νmax (CHCl3): 1798 (β-lactam C=O), 1730 (ester C=O), 1710 (sh.) (olefinic C=C)cm-1. δ (CDCl3): 2.96 (d, J 16 Hz, 1H, C(6)H), 3.34 (dd, J 16, J' 2 Hz, 1H, C(6)H), 3.36 (s, 3H, OCH3), 3.56 (s, 2H, CH2Ar), 4.60-4.90 (complex, 3H, CH2O and olefinic H), 5.25 (s, 1H, C(2)H), 5.52 (d, J 2 Hz, 1H, C(5)H), 7.22 (s, 5H, Ar-H). m/e: 234 (2%), 229 (C13H11NO3, 13%), 168 (19), 118 (12), 99 (22), 91 (100).

Workup

  1. additionwere added
  2. washwas washed with 5% sodium chloride solution (10 ml.) and saturated sodium chloride solution (10 ml.)
  3. dry with materialThe solution was dried (magnesium sulphate)
  4. customthe solvent was evaporated under reduced pressure
  5. customto yield a yellow gum

Sources & evidence

ORD record
ord-198e23e2f09140c4a2207de80a425999
Source dataset
uspto-grants-1979_09
Patent number
US04166904

Reaction notes

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