(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinone → HCID 57026143, compound

HRID 2210711Notes

Reaction equation

HRID 2210711 reaction equation
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])[CH3:11])(=O)C.[CH3:19][Si:20]([CH3:34])([CH3:33])[O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH:24]=[C:23]1[O:28][Si:29]([CH3:32])([CH3:31])[CH3:30]>>[CH2:16]([O:15][C:13]([O:12][C@@H:10]([C@@H:6]1[C@@H:5]([C@@H:24]2[CH2:25][CH2:26][CH2:27][C@@H:22]([O:21][Si:20]([CH3:33])([CH3:19])[CH3:34])[C:23]2=[O:28])[NH:8][C:7]1=[O:9])[CH3:11])=[O:14])[CH:17]=[CH2:18].[CH2:16]([O:15][C:13]([O:12][C@@H:10]([C@@H:6]1[C@@H:5]([C@H:27]2[CH2:26][CH2:25][CH2:24][C@H:23]([O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:22]2=[O:21])[NH:8][C:7]1=[O:9])[CH3:11])=[O:14])[CH:17]=[CH2:18]

Participants

4

Reactant 2

HCID 18604782(3R,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-acetoxy-2-azetidinoneHCID 19379277HCID 19379277, compound

Product 2

HCID 57026143HCID 57026143, compoundHCID 57103704HCID 57103704, compound

Procedure

Using (3R,4R)-4-acetoxy-3-[(R)-1-(allyloxycarbonyloxy)ethyl]azetidin-2-one and 1,2-bis(trimethylsilyloxy)-2-cyclohexene, the procedure of Reference Example 3 was otherwise repeated to give (3S,4R)-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-4-[(1S,3R)-2-oxo-3-trimethylsilyloxycyclohexan-1-yl]azetidin-2-one (S-compound) and (3S,4R)-3-[(R)-1-(allyloxycarbonyloxy)ethyl]-4-[(1R,3S)-2-oxo-3-trimethylsilyloxycyclohexan-1-yl]azetidin-2-one (R-compound), each as a colorless oil.

Sources & evidence

ORD record
ord-0c7f1172ffeb4b8b8fcb2189530233d4
Source dataset
uspto-grants-1995_10
Patent number
US05459260

Reaction notes

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