Ethanol → HCID 15679290, compound

HRID 1463519Notes

Reaction equation

HRID 1463519 reaction equation
CCO.[ClH:4].[NH:5]1[CH2:12][CH2:11][CH2:10][C@@H:6]1[C:7]([NH2:9])=[O:8].C([O-])([O-])=O.[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CS(C)=O>[ClH:4].[NH:5]1[CH2:12][CH2:11][CH2:10][C@@H:6]1[C:7]([NH2:9])=[O:8].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:5]2[CH2:12][CH2:11][CH2:10][C@@H:6]2[C:7]([NH2:9])=[O:8])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 46735192D-Prolinamide--hydrogen chloride (1/1)

Product 2

HCID 15679290HCID 15679290, compoundYield 117.4%HCID 46735192D-Prolinamide--hydrogen chloride (1/1)Yield 64%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(R)-Prolinamide hydrochloride was prepared according to G. Flouret et al. J. Med. Chem. 16 (1973) 1137 in a yield of 64% (lit. 53%); mp 180°-181° C. (lit. 178°-180° C.); [α]D22 =+67° (c=0.80, EtOH) (lit. [α]D23 =+69.5° (c=2, EtOH). To a mixture of (R)-prolinamide hydrochloride (4.3 g, 23 mmol) and K2CO3 (8.3 g, 60 mmol) in 20 ml dry DMSO was added a solution of p-fluorobenzylbromide (4.5 g, 23.5 mmol) in 3 ml DMSO at room temperature. The reaction mixture was stirred overnight, poured into 200 ml of ice-water and extracted twice with Et2O. The organic layer was washed with water, dried (Na2SO4) and evaporated. The residue was recrystallized from iPr2O to give 3.0 g (59%) pure title compound, mp 82°-83° C.; [α]D22 =+77° (c=0.8, CHCl3). From the mother liquor was obtained another 1.0 g (20%).

Workup

  1. custommp 180°-181° C. (lit. 178°-180° C.)
  2. extractionextracted twice with Et2O
  3. washThe organic layer was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was recrystallized from iPr2O

Sources & evidence

ORD record
ord-d05924ea367b4cc58c0705ba0cc037c6
Source dataset
uspto-grants-1994_04
Patent number
US05300660

Reaction notes

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