Triethylamine → HCID 86755023, compound

HRID 849357Notes

Reaction equation

HRID 849357 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][C@H:10]([CH3:33])[C@@H:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:34]1[C@@H:38]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:37]([C:46]([O-])=[O:47])[O:36][C:35]1([C:54]([O:56][CH2:57][CH3:58])=[O:55])[C:49]([O:51][CH2:52][CH3:53])=[O:50].C(N(CC)CC)C.[Cl-].ClC1N(C)CC[NH+]1C>C(Cl)(Cl)Cl.O>[C:1]([O:5][C:6]([CH2:8][N:9]([C@H:10]([CH3:33])[C@@H:11]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:22][CH:21]=1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:46]([C@H:37]1[C@H:38]([C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])[O:34][C:35]([C:49]([O:51][CH2:52][CH3:53])=[O:50])([C:54]([O:56][CH2:57][CH3:58])=[O:55])[O:36]1)=[O:47])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 109867151H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chlorideHCID 53763921HCID 53763921, compoundHCID 86755024HCID 86755024, compound

Product 1

HCID 86755023HCID 86755023, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

860 mg of N-(tert-butoxycarbonylmethyl)-{(1R,2R)-1-methyl-2-(4-phenoxyphenyl)-4-phenylbutyl}amine obtained in Example 50, 1.04 g of 5-tert-butyl 2,2-diethyl (4R,5R)-1,3-dioxolane-2,2,4,5-tetracarboxylate obtained in Example 68, and 2.02 ml of triethylamine, were dissolved in 20 ml of chloroform, and a solution of 816 mg of 2-chloro-1,3-dimethylimidazolinium chloride in 10 ml of chloroform, was added under cooling with ice, followed by stirring at the same temperature for 1 hour. The reaction solution was poured into water and extracted with ethyl acetate. The extract solution was washed with a saturated sodium chloride aqueous solution and then, dried over anhydrous sodium sulfate. The drying agent was filtered off and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain 1.45 g (yield: 95%) of the above identified compound as a colorless oily substance.

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe extract solution was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe drying agent was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)
  8. customto obtain 1.45 g (yield: 95%) of the

Sources & evidence

ORD record
ord-a1531f69c319402391e99e11030f4361
Source dataset
uspto-grants-2000_01
Patent number
US06011174

Reaction notes

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