Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Benzhydryl (E)-(2S,3S,5R)-3-(2-ethoxycarbonyl-vinyl)-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 1683165Notes

Reaction equation

[CH:1]([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]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:32])[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31](/[CH:33]=[CH:1]/[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:32])[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

500 mg (1.30 mmol) of benzhydryl (2S,3R,5R)-3-formyl-3-methyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 20 ml of THF under argon and treated with 500 mg (1.40 mmol) of ethoxycarbonylmethylene-triphenylphosphorane. The yellow solution was stirred at 50° C. for 75 minutes 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

concentrationsubsequently concentrated
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-df66eff23bf542c68a573b0aa57845c8
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637579

Reaction notes

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