tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate → 2-Oxo-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 867635Notes

Reaction equation

HRID 867635 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].[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:36])=[O:35].O.O.O.O.O.O.O.O.O.O.B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl:55][O-].[Na+]>C(Cl)Cl.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[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:18]=[C:19]1[CH:22]([N:23]([Cl:55])[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:35])=[O:36]

Participants

7

Reactant 3

HCID 13575530tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonateHCID 18377803Trisodium;borate;decahydrateHCID 23665760Sodium Hypochlorite

Product 1

HCID 1317142682-Oxo-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 62657Potassium Phosphate, TribasicSolvent

Procedure

(S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt (0.9 g; see Example 4) dissolved in 80 ml of methylene chloride is added to a mixture (cooled to 0°-5° C.) of 3.17 g of sodium borate decahydrate and 11.8 ml of a 5.25% sodium hypochlorite solution in 70 ml of water. The reaction mixture is vigorously stirred for 55 minutes while cooling in an ice bath. After diluting the mixture with 0.5M monobasic potassium phosphate solution, the product is extracted with methylene chloride (three 150 ml portions). Combination of the extracts, drying (sodium sulfate), and removal of solvent in vacuo yields the title compound as an oil (0.94 g).

Workup

  1. temperaturewhile cooling in an ice bath
  2. extractionthe product is extracted with methylene chloride (three 150 ml portions)
  3. customCombination of the extracts, drying
  4. custom(sodium sulfate), and removal of solvent in vacuo

Sources & evidence

ORD record
ord-3a610612662f45009147c2c12d656cc0
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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