1,2-Dichloroethane → HCID 54108658, compound

HRID 1738294Notes

Reaction equation

HRID 1738294 reaction equation
[CH3:1][CH:2]([CH3:13])[CH2:3][CH:4]([C:9](=[O:12])[NH:10][CH3:11])[CH2:5][C:6]([OH:8])=[O:7].[F:14][C:15]1[C:20](O)=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:16]=1[F:25].C(Cl)CCl>ClCCl>[F:14][C:15]1[C:16]([F:25])=[C:17]([F:24])[C:18]([F:23])=[C:19]([F:22])[C:20]=1[O:7][C:6](=[O:8])[CH2:5][CH:4]([C:9](=[O:12])[NH:10][CH3:11])[CH2:3][CH:2]([CH3:13])[CH3:1]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 13041PentafluorophenolHCID 23294594HCID 23294594, compound

Product 1

HCID 54108658HCID 54108658, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 5-methyl-3-methylcarbamoyl-hexanoic acid (0.40 g, 2.13 mmol) in dichloromethane (10 ml) was added pentafluorophenol (0.43 g, 2.35 mmol) and EDC (0.45 g, 2.35 mmol). The mixture was stirred at room temperature for 2 h, diluted with more dichloromethane and washed successively with 1 M Na2CO3 solution, 1M HCl and brine. The organic phase was dried (anhydrous MgSO4), filtered and evaporated to leave the title compound as an oil (0.38 g, 56%), which was used in Step D without further purification. 1H-NMR; δ (CDCl3), 5.77 (1H, m), 3.10 (1H, m), 2.83 (3H, d, J=4.7 Hz), 2.75 (2H, m), 1.70 (1H, m), 1.59 (1H, m), 1.31 (1H, m), 0.95 (3H, d, J=4.9 Hz) and 0.93 (3H, d, J=4.8 Hz).

Workup

  1. washwashed successively with 1 M Na2CO3 solution, 1M HCl and brine
  2. dry with materialThe organic phase was dried (anhydrous MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7b58c9761b024a53816ed94eb621b07d
Source dataset
uspto-grants-1999_10
Patent number
US05962529

Reaction notes

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