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 263745Notes

Reaction equation

HRID 263745 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. Yield: 157 mg (45%) of pale yellow solid IR (film): 1788, 1754, 1704, 1642 cm-1MS: (M+NH4+) 483.4 1H-NMR (400MHz, CDCl3): δ[ppm]=1.32(t,3H,J=7.1 Hz),1.38(s,3H), 2.03(d,3H,J=1.5Hz), 3.05(dd,1H,J=1.8Hz, 16Hz,6-H), 3.57(dd,1 H, J=4.3Hz, 16Hz,6-H), 4.23(q,2H,J=7.1Hz), 4.89(s,1H,2-H), 5.29(dd, 1H,J=4.3, 1.8Hz,5-H), 6.94(s,1H,CHPh2), 7.20(d,1H,J=1.5Hz,=CH), 7.30-7.36(m,10H,Ph).

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-250c347c2cda4fb482556546cf717a81
Source dataset
uspto-grants-1997_07
Patent number
US05644053

Reaction notes

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