3-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester → 3-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-4-methyl-6-[1-[[(2-methylpropoxy)carbonyl]oxy]ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

HRID 1290413Notes

Reaction equation

HRID 1290413 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:31])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]=[N+:29]=[N-:30])[O:24][CH2:23]2)[CH:17]([CH:32]([OH:34])[CH3:33])[C:16]3=[O:35])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]>O1CCCC1.ClC(OCC(C)C)=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][C:12]([C:14]2[N:15]3[CH:18]([CH:19]([CH3:31])[C:20]=2[S:21][CH:22]2[CH2:26][CH:25]([CH2:27][N:28]=[N+:29]=[N-:30])[O:24][CH2:23]2)[CH:17]([CH:32]([O:34][C:12]([O:11][CH2:10][CH:7]([CH3:8])[CH3:6])=[O:13])[CH3:33])[C:16]3=[O:35])=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 1

HCID 867503233-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-6-(1-Hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl ester

Product 1

HCID 536598553-[[5-(Azidomethyl)tetrahydro-3-furanyl]thio]-4-methyl-6-[1-[[(2-methylpropoxy)carbonyl]oxy]ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (4-nitrophenyl)methyl esterYield 106.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 62365Isobutyl chloroformateSolventHCID 2733832Lithium HexamethyldisilazideSolvent

Procedure

The title compound is prepared by the procedure of Example 185 using 1.00 g of product from Example 63 in 20 ml of tetrahydrofuran, 0.26 ml of isobutyl chloroformate and 2.2 ml of 0.1M lithium bis(trimethylsilyl)amide to give 0.636 g of the desired product after chromatography.

Sources & evidence

ORD record
ord-1d5cd0c4b09a42ce90d686986b4e8d3a
Source dataset
uspto-grants-1998_05
Patent number
US05750735

Reaction notes

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