Pyridine → (+/-)-3-[(Azidophenylacetyl)amino]-3-methoxy-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 371210Notes

Reaction equation

HRID 371210 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].[NH2:18][C:19]1([O:28][CH3:29])[CH2:22][N:21]([S:23]([O-:26])(=[O:25])=[O:24])[C:20]1=[O:27].N1C=CC=CC=1.[N:36]([CH:39]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:40](Cl)=[O:41])=[N+:37]=[N-:38].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C>[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].[N:36]([CH:39]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:40]([NH:18][C:19]1([O:28][CH3:29])[CH2:22][N:21]([S:23]([O-:26])(=[O:24])=[O:25])[C:20]1=[O:27])=[O:41])=[N+:37]=[N-:38]

Participants

6

Reactant 4

HCID 1049PyridineHCID 62657Potassium Phosphate, TribasicHCID 854292-Azido-2-phenylacetyl chlorideHCID 1317142653-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium salt

Product 1

HCID 131714272(+/-)-3-[(Azidophenylacetyl)amino]-3-methoxy-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-20 °C

Procedure

3-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium salt (202 mgs; see Example 74A) is dissolved in 20 ml of dry acetonitrile. To the well stirred solution at -20° C. under dry nitrogen are added dry pyridine (167 μl) and α-azidophenylacetyl chloride (96 μl). After 20 minutes, 0.5M pH 5.5 monobasic potassium phosphate buffer (12 ml) is added and the acetonitrile removed in vacuo. The aqueous residue is extracted three times with methylene chloride. The extract is dried over anhydrous sodium sulfate and evaporated in vacuo to give 281 mg of crude product as a gum. This is purified by chromatography through a column of silica gel (30 g) using methylene chloride and mixtures of methylene chloride-methanol up to 6% methanol, and yielding 231 mg of the title compound.

Workup

  1. customthe acetonitrile removed in vacuo
  2. extractionThe aqueous residue is extracted three times with methylene chloride
  3. dry with materialThe extract is dried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customto give 281 mg of crude product as a gum
  6. customThis is purified by chromatography through a column of silica gel (30 g)

Sources & evidence

ORD record
ord-2def93c68caa4927a395069a05e16070
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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