HCID 86752081, compound → HCID 86752080, compound

HRID 862397Notes

Reaction equation

HRID 862397 reaction equation
[C:1]([O:4][C:5]1[CH2:13][C@H:12]2[N:9]([C:10](=[O:24])[C@@H:11]2[C@H:14]([O:16][Si](C(C)(C)C)(C)C)[CH3:15])[C:8]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[O:26])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]>CO.Cl>[C:1]([O:4][C:5]1[CH2:13][C@H:12]2[N:9]([C:10](=[O:24])[C@@H:11]2[C@H:14]([OH:16])[CH3:15])[C:8]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=[O:26])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86752081HCID 86752081, compound

Product 1

HCID 86752080HCID 86752080, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-methoxybenzyl (7R,8S)-5-acetoxy-8-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-9-oxo-1-azabicyclo[5.2.0]non-2,4-diene-2-carboxylate (88 mg, 0.17 mM) in methanol (6 ml) was added hydrochloric acid (10 drops, 2N). After 6 hours the solvent was evaporated and the product purified by chromatography on silica (10 ml), eluting with ethyl acetate/dichloromethane, (1:1) to give 4-methoxybenzyl (7R,8S)-5-acetoxy-8-[(1R)-1-hydroxyethyl]-9-oxo-1-azabicyclo[5.2.0]non-2,4-diene-2-carboxylate (29 mg, 39%).

Workup

  1. customAfter 6 hours the solvent was evaporated
  2. customthe product purified by chromatography on silica (10 ml)
  3. washeluting with ethyl acetate/dichloromethane, (1:1)

Sources & evidence

ORD record
ord-b2cbc9ab1967466ebc7b42fd883e406c
Source dataset
uspto-grants-1998_02
Patent number
US05719139

Reaction notes

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