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

HRID 617596Notes

Reaction equation

HRID 617596 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-af0b40e5c2a446e5a672b91013558bb6
Source dataset
uspto-grants-1999_09
Patent number
US05948820

Reaction notes

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