Potassium Phosphate, Tribasic → 3-Methoxy-2-oxo-3-[(2-thienylacetyl)amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 371208Notes

Reaction equation

[CH2:1]([N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[CH3:18][O:19][C:20]1([NH2:29])[CH2:23][N:22]([S:24]([O-:27])(=[O:26])=[O:25])[C:21]1=[O:28].[S:30]1[CH:34]=[CH:33][CH:32]=[C:31]1[CH2:35][C:36](Cl)=[O:37].P([O-])([O-])([O-])=O.[K+].[K+].[K+].S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.N1C=CC=CC=1>[CH2:14]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16][CH3:17].[CH3:18][O:19][C:20]1([NH:29][C:36](=[O:37])[CH2:35][C:31]2[S:30][CH:34]=[CH:33][CH:32]=2)[CH2:23][N:22]([S:24]([O-:27])(=[O:26])=[O:25])[C:21]1=[O:28]

Participants

Conditions

Temperature: -10 °C

Procedure

3-Methoxy-3-amino-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt (102 mg) is dissolved in 10 ml of dry acetonitrile. Dry pyridine (56.5 μl) is added and the solution is stirred well at -10° C. under dry nitrogen. Thienylacetyl chloride (44 μl) in 1 ml of dry acetonitrile is added dropwise. In 15 minutes the reaction is complete as shown by thin layer chromatography. Potassium phosphate buffer (0.5M, pH 5.5, 4.2 ml) and tetrabutylammonium sulfate (8.5 mg, 0.1 equiv.) are added and most of the acetonitrile is removed in vacuo. The residue is diluted with water and extracted with three 20 ml portions of methylene chloride. The extract is dried over anhydrous sodium sulfate and evaporated in vacuo to yield 107 mg of a gum. The crude product is purified by chromatography on silica gel using methylene chloride-methanol, yielding 66 mg of the title compound.

Workup

customis removed in vacuo
additionThe residue is diluted with water
extractionextracted with three 20 ml portions of methylene chloride
dry with materialThe extract is dried over anhydrous sodium sulfate
customevaporated in vacuo

Sources & evidence

ORD record: ord-788c87fa6b144b1a8817597ccf11eb94
Source dataset: uspto-grants-1985_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04529698

Reaction notes

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