Diethyl Ether → HCID 23317243, compound

HRID 1982110Notes

Reaction equation

HRID 1982110 reaction equation
ClCC(C)(C)C([NH-])=O.Cl[CH2:10][C:11]([CH3:24])([CH3:23])[C:12]([NH:14]/[C:15](/[CH3:22])=[CH:16]\[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[O:13].[H-].[Na+].CCOCC>CN(C=O)C.C(Cl)Cl>[CH2:20]([O:19][C:17]([CH2:16][C:15]([N:14]1[CH2:10][C:11]([CH3:24])([CH3:23])[C:12]1=[O:13])=[CH2:22])=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 86740845HCID 86740845, compoundHCID 178446068HCID 178446068, compound

Product 1

HCID 23317243HCID 23317243, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

The β-chloropivaloyl amide cyclization to the title β-lactam compound was accomplished by treatment of 209 mg (0.84 mmole) of the amide with 64.5 mg (1.3 mmole) of NaH in 5 mL of DMF-CH2Cl2 (1:4) for 3 hours at room temperature. The reaction mixture was poured into 75 mL of ether and washed with two 25 mL portions of water, 25 mL of brine, dried over MgSO4, filtered and evaporated to yield 177 mg (0.84 mmole, 100%) of the β-lactam title compound as an oil. IR (neat) 1770, 1705 cm-1 ; 1H NMR δ 1.16-1.33 (9H, m), 2.63 (3H, s), 3.26 (2H, s), 4.03-4.26 (2H, q), 5.2 (1H, s).

Workup

  1. washwashed with two 25 mL portions of water, 25 mL of brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f9e575bc67a246cb97bceffbddd1f7b6
Source dataset
uspto-grants-1986_06
Patent number
US04595532

Reaction notes

Loading…