Ethyl Acetate → HCID 12849728, compound

HRID 1903706Notes

Reaction equation

HRID 1903706 reaction equation
[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([O:17]C=O)[CH3:16])[C:9]=1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])(=[O:3])[CH3:2].[OH-].[Na+].C(OC(=O)C)C>O1CCOCC1>[C:1]([NH:4]/[CH:5]=[CH:6]/[S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:20])[C@@H:12]2[C@H:15]([OH:17])[CH3:16])[C:9]=1[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 12849735HCID 12849735, compound

Product 1

HCID 12849728HCID 12849728, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

The formate ester (e4, 425 mg,0.89 mM) was dissolved in 20% aqueous 1,4-dioxan (80 ml) and cooled to 0° C. 0.1 N Sodium hydroxide solution (10.74 ml, 1.07 mM) was added and stirring continued for 5 minutes. Ethylacetate (150 ml) was then added and the organic solution washed with water, saturated sodium chloride solution and dried over anhydrous magnesium sulphate. After filtration, the solvent was removed to yield a pale yellow solid. This solid was chromatographed over silica gel (15 gm). Elution with 10% ethanol/chloroform gave the pure p-nitrobenzyl (5R,6S)-3-(E-2-acetamidoethenylthio)-6-[(R)-1-hydroxyethyl]-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (e5) as a white solid. This solid was digested in dry diethyl ether and collected by filtration (100 mg), λmax (EtOH) 325 nm (εm 16880), 263 nm (εm 17968), νmax (KBr) 3420, 3260, 1778, 1700, 1675, 1624, 1554, 1520, 1380, 1350, 1335 cm-1 ; δH (d7 -DMF) 10.50 (1H, d. J 10 Hz, NH), 8.30 (2H, d, aromatic protons), 7.85 (2H, d, aromatic protons), 7.22 (1H, dd, J 10 Hz and 14 Hz, NHCH=CH), 6.02 (1H, d, J 14 Hz), 5.47 (2H, q, CH2Ar), 4.28 (dt, 1H, J 3 Hz and 9 Hz, 5-CH), 4.08 (1H, dq, 8-CH), 3.43 (1H, dd, J 3 Hz and 6.3 Hz, 6-CH), 3.27 (2H, ABX, 4-CH2) 2.03 (3H, s, COCH3), 1.23 (3H, d, J 6 Hz, CH3CH).

Workup

  1. washthe organic solution washed with water, saturated sodium chloride solution
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationAfter filtration
  4. customthe solvent was removed
  5. customto yield a pale yellow solid
  6. customThis solid was chromatographed over silica gel (15 gm)
  7. washElution with 10% ethanol/chloroform

Sources & evidence

ORD record
ord-1679c8e2a46c4e5aa6a352ed431ff888
Source dataset
uspto-grants-1984_03
Patent number
US04438036

Reaction notes

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