Triethylamine → HCID 22464496, compound

HRID 1935451Notes

Reaction equation

HRID 1935451 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C:12]([F:15])([F:14])[F:13].[O:16](C(OC(C)(C)C)=O)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=O.CCN(CC)CC>CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:17]([NH:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C:12]([F:15])([F:13])[F:14])([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:16]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 22464484HCID 22464484, compound

Product 1

HCID 22464496HCID 22464496, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-aminomethyl-(2,2,2-trifluoroethylthio)benzene hydrochloride (500 mg, 1.94 mmol) in CH2C2 (20 mL) were added successively (BOC)2O (465 mg, 2.13 mmol), DMAP (23.7 mg, 0.194 mmol) and Et3N (0.27 mL, 1.94 mmol). The reaction mixture was stirred overnight at room temperature and was then diluted with EtOAc and washed successively with 10% aqueous citric acid, brine, and water. The organic layer was dried over MgSO4 and concentrated at reduced pressure. Silica gel chromatography (isocratic elution with 20% EtOAc-hexanes) afforded the title compound as a colorless oil:

Workup

  1. washwashed successively with 10% aqueous citric acid, brine, and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated at reduced pressure
  4. washSilica gel chromatography (isocratic elution with 20% EtOAc-hexanes)

Sources & evidence

ORD record
ord-af9a6d24c60c4c2b813a81b57ea45bc9
Source dataset
uspto-grants-2002_05
Patent number
US06387911B1

Reaction notes

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