Azetidon → (3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-{2-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl) thien-2-yl]-2-oxoethyl}azetidin-2-one

HRID 1271115Notes

Reaction equation

HRID 1271115 reaction equation
[C:1]([Si:5]([CH3:21])([CH3:20])[O:6][CH2:7][C:8]1[S:9][C:10]([C:13]([O:15][Si](C)(C)C)=[CH2:14])=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].C([O:25][C@@H:26]1[C@@H:29]([C@H:30]([O:32][Si:33]([C:36]([CH3:39])([CH3:38])[CH3:37])([CH3:35])[CH3:34])[CH3:31])[C:28](=O)[NH:27]1)(=O)C>>[Si:33]([O:32][C@@H:30]([C@@H:29]1[C@@H:28]([CH2:15][C:13]([C:10]2[S:9][C:8]([CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:20])[CH3:21])=[CH:12][CH:11]=2)=[O:14])[NH:27][C:26]1=[O:25])[CH3:31])([C:36]([CH3:39])([CH3:37])[CH3:38])([CH3:35])[CH3:34]

Participants

3

Reactant 2

HCID 10935078AzetidonHCID 58844233Tert-butyl(dimethyl)[(5-{1-[(trimethylsilyl)oxy]vinyl}thien-2-yl)methoxy]silane

Product 1

HCID 58844185(3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-{2-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl) thien-2-yl]-2-oxoethyl}azetidin-2-one

Procedure

In the same manner as reference example 3, from tert-butyl(dimethyl)[(5-{1-[(trimethylsilyl)oxy]vinyl}thien-2-yl)methoxy]silane prepared in the above step and (2R,3R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxo-2-azetidinyl acetate (20.99 g), there was obtained (3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-{2-[5-({[tert-butyl(dimethyl)silyl]oxy}methyl) thien-2-yl]-2-oxoethyl}azetidin-2-one (10.32 g).

Sources & evidence

ORD record
ord-32abc2e5a3f641ce9dfe86a1a76cd2ad
Source dataset
uspto-grants-2007_04
Patent number
US07205291B2

Reaction notes

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