Pyridine → 3-[[1,3-Dioxo-2-phenyl-3-(phenylmethoxy)propyl]amino]-3-methoxy-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 371206Notes

Reaction equation

HRID 371206 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.[CH2:36]([O:43][C:44]([CH:46]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:47](Cl)=[O:48])=[O:45])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C(#N)C.C(Cl)Cl>[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].[O:48]=[C:47]([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])[CH:46]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:44](=[O:45])[O:43][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 62657Potassium Phosphate, TribasicHCID 21289869Benzyl (chlorocarbonyl)phenylacetateHCID 1317142653-Amino-3-methoxy-2-oxo-1-azetidinesulfonic acid tetrabutylammonium salt

Product 1

HCID 1317142693-[[1,3-Dioxo-2-phenyl-3-(phenylmethoxy)propyl]amino]-3-methoxy-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium saltYield 69.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

Crude 3-amino-3-methoxy-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium salt (431 mg, see Example 74), containing borax, is dissolved in 30 ml of dry acetonitrile. Dry pyridine (317 μl) is added and the solution stirred well at -10° C. under dry nitrogen. α-(Benzyloxycarbonyl)phenylacetyl chloride (568 mg) in 3 ml of dry acetonitrile is added dropwise. Thin layer chromatography indicates the reaction to be complete after 15 minutes. Potassium phosphate buffer (0.5M, pH 5.5, 17 ml) is added and most of the acetonitrile is removed in vacuo. The residue is diluted with water and extracted three times with equal volumes of methylene chloride. The extract is dried over anhydrous sodium sulfate and evaporated in vacuo to give 1.032 g of crude product, which is dissolved in 3 ml of methylene chloride and chromatographed on a silica column using methylene chloridemethanol to give 470 mg of the title compound.

Workup

  1. customthe reaction
  2. customis removed in vacuo
  3. additionThe residue is diluted with water
  4. extractionextracted three times with equal volumes of methylene chloride
  5. dry with materialThe extract is dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customto give 1.032 g of crude product, which
  8. customchromatographed on a silica column

Sources & evidence

ORD record
ord-f58f009ab87a4a5da6f6881b33d50e5e
Source dataset
uspto-grants-1985_07
Patent number
US04529698

Reaction notes

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