(3S-trans)-3-[(t-butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt → (2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

HRID 851632Notes

Reaction equation

HRID 851632 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.C(OC([NH:25][C@H:26]1[C@H:29]([CH3:30])[N:28]([S:31]([O-:34])(=[O:33])=[O:32])[C:27]1=[O:35])=O)(C)(C)C>O>[NH2:25][C@H:26]1[C@@H:29]([CH3:30])[N:28]([S:31]([OH:34])(=[O:32])=[O:33])[C:27]1=[O:35]

Participants

3

Reactant 1

HCID 13146192(3S-trans)-3-[(t-butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

Product 1

HCID 11084475(2R,3S)-3-Amino-2-methyl-4-oxo-1-azetidinesulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following the procedure of example 2D, but substituting (3S-cis)-3-[(t-butoxycarbonyl)-amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt for (3S-trans)-3-[(t-butoxycarbonyl)amino]-4-methyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt yields the title compound, melting point 200° C., dec., [α]D21 =-61.8°[c=5.1, water].

Sources & evidence

ORD record
ord-935f0cd0dd954a5697d2d6a331af1896
Source dataset
uspto-grants-1983_05
Patent number
US04386034

Reaction notes

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