Chloromethyl pivalate → HCID 70547462, compound

HRID 851444Notes

Reaction equation

HRID 851444 reaction equation
[C:1]1([C@@H:7]2[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C@H:9]([C:22]([OH:24])=[O:23])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].[K+].[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C)C=O.C(OCC)(=O)C>[C:1]1([C@@H:7]2[CH2:11][N:10]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[C@H:9]([C:22]([O:24][CH2:34][O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])=[O:23])[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 87885Chloromethyl pivalateHCID 522689Potassium FluorideHCID 53666284HCID 53666284, compound

Product 1

HCID 70547462HCID 70547462, compoundYield 102.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(cis)-4-Phenyl-1-phenylmethoxycarbonyl-L-proline (3.52 g), dissolved in 25 ml of dry dimethylformamide, is treated with 1.61 g of anhydrous potassium fluoride and 2.0 g of chloromethyl pivalate under argon at room temperature for about 16 hours. The reaction mixture is diluted with ethyl acetate and washed with water (three times), saturated sodium bicarbonate and saturated brine. The aqueous layers are backwashed with fresh ethyl acetate. The combined organic layers are dried (MgSO4) and concentrated in vacuo to give 4.86 g of an oil.

Workup

  1. washwashed with water (three times), saturated sodium bicarbonate and saturated brine
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-640dce03dd2e44c883630f7daeecf774
Source dataset
uspto-grants-1983_05
Patent number
US04384123

Reaction notes

Loading…