HCID 86749053, compound → HCID 57010825, compound

HRID 2210714Notes

Reaction equation

HRID 2210714 reaction equation
[OH:1][C@H:2]1[C:12]2[C@@H:6]([C@H:7]3[N:10]([C:11]=2[C:13]([O-:15])=[O:14])[C:9](=[O:16])[C@@H:8]3[C@H:17]([OH:19])[CH3:18])[O:5][CH2:4][CH2:3]1.[Na+].O[C@@H:22]([C@@H:24]1[C@@H]2N(C(C([O-])=O)=C3[C@@H]2CCC[C@@H]3CCOC(=O)C2C=CC=NC=2)C1=O)[CH3:23].[Na+]>C1(C)C=CC=CC=1>[OH:1][C@H:2]1[C:12]2[C@@H:6]([C@H:7]3[N:10]([C:11]=2[C:13]([O:15][CH2:24][CH:22]=[CH2:23])=[O:14])[C:9](=[O:16])[C@@H:8]3[C@H:17]([OH:19])[CH3:18])[O:5][CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 86749053HCID 86749053, compoundHCID 86749054HCID 86749054, compound

Product 1

HCID 57010825HCID 57010825, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Sodium (5S,6S, 7S, 11R)-11-hydroxy-5-[(R)-1-hydroxyethyl]-4-oxo-8-oxa-3-azatricyclo[5.4.0.03,6 ]undec-1-ene -2-carboxylate ##STR54## (1) A solution of the compound obtained in Reference Example 29 (220 mg) in toluene (5 ml) was stirred at 50° C. for 4 hours and, then, at 80° C. for 8 hours. The solvent was then distilled off under reduced pressure and the residue was subjected to silica gel column chromatography (70-230 mesh, 20 g; ethyl acetate-hexane =1:2) to give allyl (5S,6S,7S,11R)-11-hydroxy-5-[(R) -1-hydroxyethyl]-4-oxo-8-oxa-3azatricyclo[5.4.0.03,6 ]undec-1-ene-2-carboxylate (R2 =CH2CH=CH2) (93 mg).

Workup

  1. waitat 80° C. for 8 hours
  2. distillationThe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-f1e1ea5bffbf474e82d1dc9499bbcfc1
Source dataset
uspto-grants-1995_10
Patent number
US05459260

Reaction notes

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