Water → HCID 13471582, compound

HRID 2413887Notes

Reaction equation

HRID 2413887 reaction equation
C(N(S(F)(F)[F:7])CC)C.[F-].[K+].[CH2:12]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[NH:25][C:24](=[O:26])[CH:23]1[C:27](O)([CH3:29])[CH3:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>ClCCl>[CH2:12]([O:19][C:20](=[O:31])[CH2:21][CH:22]1[NH:25][C:24](=[O:26])[CH:23]1[C:27]([F:7])([CH3:29])[CH3:28])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 522689Potassium FluorideHCID 70417261HCID 70417261, compound

Product 1

HCID 13471582HCID 13471582, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a -78° cold solution of 3 ml of diethylaminosulphurtrifluoride and 1.7 g of potassium fluoride in 80 ml of dichloromethane is added a solution of 3.2 g of (3SR,4RS)-3-(1-hydroxy-1-methyethyl)-2-oxoazetidine-4-yl acetic acid benzylester in 170 ml of dichloromethane. This mixture is stirred for 15 minutes at -78° and then mixed with water. After addition of further dichloromethane the phases are separated and the organic phase washed with saturated NaCl, dried over MgSO4 and evaporated to dryness. Chromatography of the residue over silica gel (ethylacetate/cyclohexane=1/1) yields the title compound m.p. 112°-116°.

Workup

  1. customare separated
  2. washthe organic phase washed with saturated NaCl
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-bd95f4e17c674df3971376ee2a364341
Source dataset
uspto-grants-1988_01
Patent number
US04720490

Reaction notes

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