Tetrahydrofuran → Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 1683168Notes

Reaction equation

HRID 1683168 reaction equation
C([C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])=O.[CH2:28]([O:30][C:31]([C:33](=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:34])=[O:32])[CH3:29].[CH2:54]1COCC1>>[CH2:28]([O:30][C:31](/[C:33](/[CH3:34])=[CH:54]/[C@:3]1([CH3:27])[S:9][C@H:8]2[N:5]([C:6](=[O:10])[CH2:7]2)[C@H:4]1[C:11]([O:13][CH:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:12])=[O:32])[CH3:29]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 79792Ethyl 2-(triphenylphosphoranylidene)propionateHCID 10762402benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Product 1

HCID 86750937Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-propenyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Conditions

Temperature
70 °C

Procedure

286 mg (0.75 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptan-2-carboxylate were dissolved in 12 ml of THF under argon and treated with 271 mg (0.75 mmol) of (1-ethoxycarbonylethylidene)-triphenylphosphorane. The yellow solution was stirred at 70° C. for 6 hours and subsequently concentrated. The residue remaining behind was chromatographed over silica gel (0.040-0.063 mm particle size) with ethyl acetate:hexane (9:16) as the eluent.

Workup

  1. concentrationsubsequently concentrated
  2. customThe residue remaining behind was chromatographed over silica gel (0.040-0.063 mm particle size) with ethyl acetate:hexane (9:16) as the eluent

Sources & evidence

ORD record
ord-d7bbbc56be2d475699b99816be80c272
Source dataset
uspto-grants-1997_06
Patent number
US05637579

Reaction notes

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