Diethyl Ether → HCID 178467627, compound

HRID 867588Notes

Reaction equation

HRID 867588 reaction equation
C[Li].[N+:3]([C:6]1[CH:49]=[CH:48][CH:47]=[CH:46][C:7]=1[CH2:8][O:9][C:10]([CH:12]([PH:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:13]1[CH:16]([CH2:17][C:18]([C:20]2C=CC=CC=2)=S)[CH2:15][C:14]1=[O:26])=[O:11])([O-:5])=[O:4].[NH4+].[Cl-].CC[O:54]CC>C1COCC1.C(Cl)Cl>[N+:3]([C:6]1[CH:49]=[CH:48][CH:47]=[CH:46][C:7]=1[CH2:8][O:9][C:10]([CH:12]([PH:27]([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[N:13]1[CH:16]([CH2:17][C:18]([CH3:20])=[O:54])[CH2:15][C:14]1=[O:26])=[O:11])([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 178418348HCID 178418348, compoundHCID 178525171HCID 178525171, compound

Product 1

HCID 178467627HCID 178467627, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Cuprous iodide (0.380 g) is suspended in 10 ml anhydrous ether under N2, in a dry flask and cooled to 0°. Methyl lithium (3.0 ml, 1.3 Molar) is added dropwise and the mixture is stirred at 0° for 5 min to give a yellow suspension. The mixture is then cooled to -50°. 1-(o-nitrobenzyloxycarbonyl-triphenylphosphoranylmethyl)-4-(phenylthiocarbonylmethyl)-2-azetidinone (0.674 g) in 10 ml THF is added dropwise over 5 min. The mixture is stirred at -50° for 5 min and allowed to come to -20° over 20 min and stirred at -20° for 5 min. Saturated NH4Cl solution 5 ml is added and the mixture is diluted with CH2Cl2. Stirred at r.t. for 5 min. The organic phase is separated, dried and evaporated. The residue is chromatographed on silica gel using EtOAc as eluant to give 0.162 g of the product 0.112 g of recovered thio ester.

Workup

  1. temperaturecooled to 0°
  2. customto give a yellow suspension
  3. temperatureThe mixture is then cooled to -50°
  4. stirringThe mixture is stirred at -50° for 5 min
  5. waitto come to -20° over 20 min
  6. stirringstirred at -20° for 5 min
  7. stirringStirred at r.t. for 5 min
  8. customThe organic phase is separated
  9. customdried
  10. customevaporated
  11. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6dde5a04b081431cbbea257b30887989
Source dataset
uspto-grants-1988_10
Patent number
US04775669

Reaction notes

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