Triethylamine → (3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylamino)nonyl]chroman

HRID 1792414Notes

Reaction equation

HRID 1792414 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[C:20]2[C:15](=[CH:16][C:17]([O:21][CH2:22][O:23][CH3:24])=[CH:18][CH:19]=2)[O:14][CH2:13][C:12]1([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:28][CH:27]=1)[CH3:25].[F:36][C:37]([F:49])([C:45]([F:48])([F:47])[F:46])[CH2:38][CH2:39][CH2:40]S(Cl)(=O)=O.C(N(CC)CC)C>C(Cl)Cl>[CH3:24][O:23][CH2:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([CH:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][NH:1][CH2:40][CH2:39][CH2:38][C:37]([F:49])([F:36])[C:45]([F:48])([F:47])[F:46])[C:12]([C:26]3[CH:27]=[CH:28][C:29]([O:32][CH2:33][O:34][CH3:35])=[CH:30][CH:31]=3)([CH3:25])[CH2:13][O:14]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219731904,4,5,5,5-Pentafluoropentane-1-sulfonyl chlorideHCID 220332874-(9-Aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 22033238(3RS,4RS)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methyl-4-[9-(4,4,5,5,5-pentafluoropentylamino)nonyl]chromanYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

4-(9-aminononyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (82.3 mg, 0.17 mmol) was dissolved in 5 ml of methylenechloride under argon atmosphere, which was then cooled down to 0° C. 4,4,5,5,5-pentafluoropentylsulfonyl chloride (110.4 mg, 0.42 mmol) in 1 ml of methylene chloride and triethylamine (0.07 ml, 0.5 mmol) was added thereto, and the mixture was stirred at the same temperature for 30 minutes. The reaction was quenched with water, and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was subject to flash chromatography in silica gel (n-hexane:ethyl acetate=5:1) to give the title compound (81 mg, yield: 67%) as a colorless oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8a2c55af2e3b4a24ae2a63540a9262c5
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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