Triethylamine → HCID 15489616, compound

HRID 1870962Notes

Reaction equation

HRID 1870962 reaction equation
[C:1]1([C:7]2[CH:16]=[C:15]([C:17]([OH:19])=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH2:47][C@@H:48]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:49][OH:50].C(N(CC)CC)C>C(Cl)Cl>[OH:50][CH2:49][C@@H:48]([NH:47][C:17]([C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:16]=1)=[O:19])[CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8593CinchophenHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 447213phenylalaninol, (S)-

Product 1

HCID 15489616HCID 15489616, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-phenyl-4-quinoline-carboxylic acid (0.33 g, 1.3 mmol, Aldrich Chemical Company) in methylene chloride (5 mL) was added benzotriazol-1-yloxytris-(dimethyamino)phosphoniumhexafluorophosphate (BOP) (0.63 g, 1.43 mmol). The resulting mixture was shaken at room temperature for 5 min. (S)-(-)-2-arnino-3-phenyl-1-propanol (0.2 g, 1.3 mmol) was added along with triethylamine (0.2 mL, 1.43 mmol). The resulting mixture was shaken at room temperature for 24 h. Methylene chloride (10 mL) was added and the organic layer was washed with NaHCO3, H2O, brine, dried (MgSO4), filtered, and concentrated in vacuo to give an oil. The oil was purified by flash chromatography (silica gel, 30-80% EtOAc/hexane) to yield the title compound as a white solid (0.3 g, 60%). MS (ES+) m/e 383.5 [M+H]+, 405 [M+Na]+, 787 [2M+Na]+.

Workup

  1. washthe organic layer was washed with NaHCO3, H2O, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give an oil
  6. customThe oil was purified by flash chromatography (silica gel, 30-80% EtOAc/hexane)

Sources & evidence

ORD record
ord-781c52d5d0384fa887eda78d3f35f1bc
Source dataset
uspto-grants-2000_08
Patent number
US06100267

Reaction notes

Loading…