Chlorine → HCID 70448571, compound

HRID 1719268Notes

Reaction equation

[Si:1]([O:8][C@H:9]([C@@H:11]1[C@@H:14](SC)[N:13]([C:17](=[C:22]([CH3:24])[CH3:23])[C:18]([O:20][CH3:21])=[O:19])[C:12]1=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl:26]Cl>ClCCl.C(Cl)(Cl)(Cl)Cl>[Si:1]([O:8][C@H:9]([C@@H:11]1[C@@H:14]([Cl:26])[N:13]([C:17](=[C:22]([CH3:24])[CH3:23])[C:18]([O:20][CH3:21])=[O:19])[C:12]1=[O:25])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of methyl 2-[(3S,4R)-3-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methylthio-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (60 mg) in dichloromethane (2 ml) was added a solution of chlorine (24 mg) in carbon tetrachloride (0.2 ml) at -50° C. The solution was allowed to warm to -10° C. during 30 minutes and cooled to -50° C. An additional solution of chlorine (12 mg) in carbon tetrachloride (0.1 ml) was added. The solution was allowed to warm to -5° C. and evaporated. The residue was chromatographed on silica gel (1.5 g, eluting with 8-10% ethyl acetate in hexane) to give 21.0 mg (36.1%) of methyl 2-[(3S,4R)-3-[(1S)-1-(tert-butyldimethylsilyloxy)ethyl]-4-chloro-2-oxoazetidin-1-yl]-3-methylbut-2-enoate. NMR (CDCl3)δ: 0.12 (s, 6H), 0.93 (s, 9H), 1.34 (d, J=6.5 Hz, 3H), 2.01 (s, 3H), 2.29 (s, 3H), 3.56 (dd, J=1.5, 5 Hz, 1H), 3.77 (s, 3H), 4.30 (dq, J=5, 6.5 Hz, 1H), 5.80 (d, J=1.5 Hz, 1H).

Workup

temperaturecooled to -50° C
temperatureto warm to -5° C.
customevaporated
customThe residue was chromatographed on silica gel (1.5 g, eluting with 8-10% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-fecc0f9bee564593ad518963660fcb78
Source dataset: uspto-grants-1985_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04539152

Reaction notes

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