Hydrochloric Acid → HCID 20610320, compound

HRID 433836Notes

Reaction equation

HRID 433836 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:17]=[C:16]([CH2:18]Br)[O:15][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:22][C:23](=[O:26])[CH2:24][NH2:25])[CH3:21].[C:27]1([C:33]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=NCC(O)=O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[K+].Cl>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:17]=[C:16]([CH2:18][CH:24]([N:25]=[C:33]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:23]([O:22][CH2:20][CH3:21])=[O:26])[O:15][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 20610321HCID 20610321, compoundHCID 22398092HCID 22398092, compound

Product 1

HCID 20610320HCID 20610320, compoundYield 45.1%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

2-(5-Bromomethyl-isoxazol-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (1.0 g, 3 mmol) and N-(diphenylmethylene)glycine glycine ethyl ester (1.0 g, 3.74 mmol) were dissolved in toluene (10 mL). Aqueous potassium hydroxide, 18M, (0.25 mL, 4.5 mmol) and tetrabutylammonium bromide (97 mg, 0.30 mmol) were added. After the reaction was stirred at room temperature for 1 hour, 1N hydrochloric acid was added (4.5 mL). The organic phase was extracted with 1N hydrochloric acid, saturated sodium bicarbonate, and brine. The organic portion was dried over magnesium sulfate and the solvent removed in vacuo. The residue was chromatographed with 15% ethylacetate in hexanes on a Biotage 40S column to give the title compound (700 mg, 45%). MS (CI) m/z 518.0 (M+1).

Workup

  1. extractionThe organic phase was extracted with 1N hydrochloric acid, saturated sodium bicarbonate, and brine
  2. dry with materialThe organic portion was dried over magnesium sulfate
  3. customthe solvent removed in vacuo
  4. customThe residue was chromatographed with 15% ethylacetate in hexanes on a Biotage 40S column

Sources & evidence

ORD record
ord-1aa3e980b4314775bc2114d92a05ea5e
Source dataset
uspto-grants-2003_12
Patent number
US06668527B2

Reaction notes

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