Ethyl Acetate → HCID 14012594, compound

HRID 1940880Notes

Reaction equation

HRID 1940880 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([N:14]2[CH2:18][CH:17]([S:19][CH:20]([CH:36]([CH:38]3[CH:41]([CH:42]([O:44][Si:45]([C:48]([CH3:51])([CH3:50])[CH3:49])([CH3:47])[CH3:46])[CH3:43])[C:40](=[O:52])[NH:39]3)[CH3:37])C(=O)C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:16][CH:15]2[C:53]([N:55]([CH3:57])[CH3:56])=[O:54])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:58]([O:61][CH2:62][CH3:63])(=[O:60])[CH3:59]>ClCCl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][C:63]([CH2:62][O:61][C:58]([C:59]2[N:39]3[CH:38]([CH:36]([CH3:37])[C:20]=2[S:19][CH:17]2[CH2:16][CH:15]([C:53]([N:55]([CH3:57])[CH3:56])=[O:54])[N:14]([C:12]([O:11][CH2:10][C:7]4[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=4)=[O:13])[CH2:18]2)[CH:41]([CH:42]([O:44][Si:45]([C:48]([CH3:49])([CH3:51])[CH3:50])([CH3:46])[CH3:47])[CH3:43])[C:40]3=[O:52])=[O:60])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 2

HCID 8857Ethyl AcetateHCID 54426254HCID 54426254, compound

Product 1

HCID 14012594HCID 14012594, compound

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Titanium tetrachloride (3.12 ml of a 1.0M solution in dichloromethane) is added to 1.5 ml of dry tetrahydrofuran under argon at .room temperature. To this mixture is added [2S-[2Alpha,4alpha[R*(or S*)-[1S*,1[2R*,3R*, -3(S*)]]]]]-2-[(dimethylamino)carbonyl]-4-[[1-[1-[3-[1-[[(1,1-di-methylethyl)dimethylsilyl]oxy]ethyl]-4-oxo-2-azetidinyl]ethyl]-3-[(4-nitrophenyl)methoxy]-2,3-dioxopropyl]thio]-1-pyrrolidinecarboxylic acid (4-nitrophenyl)methyl ester (0.392 g) in 2.5 ml of tetrahydrofuran. After 30 minutes the reaction mixture is treated with ice-cold saturated sodium bicarbonate solution and ethyl acetate. The aqueous layer is extracted with ethyl acetate. The combined organic layer is washed with three portions of brine, dried over anhydrous sodium sulfate and by anhydrous magnesium sulfate. Filtration and concentration affords the crude carbapenem which is purified via silica gel chromatography (80% ethyl acetate hexanes). The title compound is obtained as a pale yellow oil (0.295 g) 77%.

Workup

  1. customroom temperature
  2. extractionThe aqueous layer is extracted with ethyl acetate
  3. washThe combined organic layer is washed with three portions of brine
  4. dry with materialdried over anhydrous sodium sulfate and by anhydrous magnesium sulfate
  5. filtrationFiltration and concentration
  6. customaffords the crude carbapenem which
  7. customis purified via silica gel chromatography (80% ethyl acetate hexanes)

Sources & evidence

ORD record
ord-6b2755f8324e46e8a94c1dca7f189427
Source dataset
uspto-grants-1997_12
Patent number
US05700930

Reaction notes

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