Water → (2S,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 1979899Notes

Reaction equation

C([N+](CCCC)(CCCC)CCCC)CCC.COC([NH:22][C@H:23]1[C@H:26]([CH3:27])[N:25]([S:28]([O-:31])(=[O:30])=[O:29])[C:24]1=[O:32])=O.C(N(CC)CC)C.Cl[SiH](Cl)Cl.O>ClCCl.C(O)=O>[NH2:22][C@H:23]1[C@H:26]([CH3:27])[N:25]([S:28]([OH:31])(=[O:29])=[O:30])[C:24]1=[O:32]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 479 mg (0.001 mole) of (3S-trans)-3-methoxycarbonylamino-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt in 10 ml of dichloromethane is treated with 139 μl of triethylamine and 112 μl of trichlorosilane. The resulting solution is refluxed for 3 hours and cooled to 0° C. Triethylamine (139 μl) and 0.5 ml of water are added, and the solution is stirred overnight. The resulting slurry is diluted with 20 ml of formic acid, stirred for 1 hour, and the solid filtered to give 117 mg of (3S-trans)-3-amino-4-methyl-2-oxo-1-azetidinesulfonic acid, inner salt.

Workup

temperatureThe resulting solution is refluxed for 3 hours
stirringstirred for 1 hour
filtrationthe solid filtered

Sources & evidence

ORD record: ord-dbff2b04bbe941b5bbea511ca60bda94
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04483797

Reaction notes

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