(2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(5-hydroxymethyl-imidazol-1-yl)ethyl]pyrrolidine → allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 975721Notes

Reaction equation

HRID 975721 reaction equation
[N+](=[C:3]([C:10](=O)[C@@H:11]([C@@H:13]1[C@@H:16]([C@H:17]([OH:19])[CH3:18])[C:15](=[O:20])[NH:14]1)[CH3:12])[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[N-].C([S:25][C@@H:26]1[CH2:30][N:29]([C:31]([O:33][CH2:34][CH:35]=[CH2:36])=[O:32])[C@H:28]([CH2:37][CH2:38][N:39]2[C:43]([CH2:44][OH:45])=[CH:42][N:41]=[CH:40]2)[CH2:27]1)(=O)C>>[CH2:34]([O:33][C:31]([N:29]1[CH2:30][C@@H:26]([S:25][C:10]2[C@H:11]([CH3:12])[C@H:13]3[N:14]([C:15](=[O:20])[C@@H:16]3[C@H:17]([OH:19])[CH3:18])[C:3]=2[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])[CH2:27][C@H:28]1[CH2:37][CH2:38][N:39]1[C:43]([CH2:44][OH:45])=[CH:42][N:41]=[CH:40]1)=[O:32])[CH:35]=[CH2:36]

Participants

3

Reactant 2

HCID 54235556(2R,4S)-1-allyloxycarbonyl-4-acetylthio-2-[2-(5-hydroxymethyl-imidazol-1-yl)ethyl]pyrrolidineHCID 54331596(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[(R)-1-methyl-3-diazo-3-allyloxycarbonyl-2-oxopropyl]-2-azetidinone

Product 1

HCID 57072749allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 59.6%

Procedure

Allyl (4R)-2-diazo-4-[(2R,3S)-3-{(1R)-1-hydroxyethyl}-4-oxoazetidin-2-yl]-3-oxopentanoate (709 mg) and (2R,4S)-4-acetylthio-1-allyloxycarbonyl-2-[2-(5-hydroxymethylimidazol-1-yl) ethyl]pyrrolidine (849 mg) were reacted in substantially the same manner as that of Example 2-3) to give allyl (4R,5S,6S)-3-[(2R,4S)-1-allyloxycarbonyl-2-{2-(5-hydroxymethylimidazol-1-yl)ethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (802 mg) as a yellow solid.

Sources & evidence

ORD record
ord-d665bc5367134d94b6de5734032ba8fb
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

Loading…