Potassium Phosphate, Tribasic → HCID 54455949, compound

HRID 1156745Notes

Reaction equation

HRID 1156745 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][C@H:11]2[CH2:14][N:13]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:12]2=[O:23])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Li+].Cl[O:28][C:29](C)(C)C.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CO.O1CCCC1>[CH3:29][O:28][C:11]1([NH:10][C:8](=[O:9])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:14][N:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]1=[O:23]

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 521297Tert-Butyl hypochloriteHCID 4177230Lithium methanolateHCID 13036861HCID 13036861, compound

Product 1

HCID 54455949HCID 54455949, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (S)-3-[(phenylacetyl)amino]-1-[(phenylmethyl)oxy]-2-azetidinone (1mM; see example 4B) in freshly distilled tetrahydrofuran (10 ml) at -78° C. is added via syringe a solution of lithium methoxide (3mM) in dry methanol (5 ml). After 5 minutes, t-butyl hypochlorite (130 μl) is added and the mixture is stirred at -78° C. for 30 minutes. The reaction mixture is poured into 0.5 M monobasic potassium phosphate buffer and extracted with two 100 ml portions of methylene chloride. The combined organic extracts are dried over sodium sulfate and concentrated to an oily residue. The title compound is isolated by column chromatography as a racemate.

Workup

  1. extractionextracted with two 100 ml portions of methylene chloride
  2. dry with materialThe combined organic extracts are dried over sodium sulfate
  3. concentrationconcentrated to an oily residue

Sources & evidence

ORD record
ord-1dbed1589dd2481bac5f802c6877aeb1
Source dataset
uspto-grants-1982_06
Patent number
US04337197

Reaction notes

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