Triethylamine → 2-[(S)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

HRID 842279Notes

Reaction equation

HRID 842279 reaction equation
[NH2:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1)[CH2:3][OH:4].C(N(CC)CC)C.[CH3:28][O:29][C@@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31](Cl)=[O:32]>C(Cl)Cl>[CH3:28][O:29][C@:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:34]([F:37])([F:36])[F:35])[C:31]([NH:1][CH:2]([CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:11][CH:12]=1)[CH2:3][OH:4])=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2724611alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, (S)-(+)-HCID 100642062-Amino-4-(4-octylphenyl)butan-1-ol

Product 1

HCID 701463422-[(S)-alpha-methoxy-alpha-trifluoromethylphenylacetylamino]-4-(4-octylphenyl)butanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Amino-4-(4-octylphenyl)butanol (30 mg), N,N-dimethyl-p-aminopyridine (52.6 mg), anhydrous triethylamine (34.2 μl) and anhydrous methylene chloride (1 ml) were mixed and the mixture was stirred under a nitrogen atmosphere at room temperature. Thereto was added (S)-α-methoxy-α-trifluoromethylphenylacetyl chloride (50.4 μl) and the mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained was purified by thin layer chromatography (eluent; chloroform:methanol=9:1) to give the two diastereomer mixtures. Moreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute) to give the subject oily substance (31.6 mg) of 67.8 minutes at retention time and the subject oily substance (31.9 mg) of 71.6 minutes at retention time.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by thin layer chromatography (eluent; chloroform:methanol=9:1)
  5. customto give the two diastereomer mixtures
  6. customMoreover, the mixture was purified by high performance liquid chromatography (eluent; methanol:water=88:12, flow rate; 8.0 ml /minute)
  7. customto give the subject oily substance (31.6 mg) of 67.8 minutes at retention time
  8. customthe subject oily substance (31.9 mg) of 71.6 minutes

Sources & evidence

ORD record
ord-7f5a9154fb1941be840a92e1b56baf0b
Source dataset
uspto-grants-2002_04
Patent number
US06372800B1

Reaction notes

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