Triethylamine → HCID 58007583, compound

HRID 1094440Notes

Reaction equation

HRID 1094440 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)[CH:2]=1.[C:24]([O:27][C:28](=O)[C@H:29](C1C=CC=CC=1)[OH:30])(=[O:26])[CH3:25].[I-].Cl[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][N+]=1C.[CH3:47]CN(CC)CC>C(Cl)Cl>[C:40]1([C@H:28]([O:27][C:24](=[O:26])[CH3:25])[C:29](=[O:30])[N:11]([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=2)[CH:47]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 58007561HCID 58007561, compoundHCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007583HCID 58007583, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.32 mmol Quinolin-3-yl-[2-(4-trifluoromethyl-phenyl)-ethyl]-amine in dry CH2Cl2 was added 0.35 mmol (+)-O-Acetyl-L-Mandelic Acid, 0.35 mmol 2-chloro-1-methylpyridinium iodide and 0.63 mmol of Et3N and the reaction mixture stirred for 16 h at rt. The solution was washed once with a saturated NaHCO3 solution and once with water. The washings were extracted once with dichloromethane. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil (155 mg) was used directly for the next step.

Workup

  1. washThe solution was washed once with a saturated NaHCO3 solution and once with water
  2. extractionThe washings were extracted once with dichloromethane
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d36d05fe37346c3b328fc6704489001
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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