Triethylamine → HCID 57938828, compound

HRID 1436493Notes

Reaction equation

HRID 1436493 reaction equation
[C:1](N1C=CN=C1)(=[O:3])[CH3:2].C(N(CC)CC)C.[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[C@@H:29]([OH:41])[C@@H:30]([NH2:40])[CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)=[O:22])([CH3:19])([CH3:18])[CH3:17]>ClCCl.C(OCC)(=O)C>[C:16]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:24]1[C@@H:29]([OH:41])[C@@H:30]([NH:40][C:1](=[O:3])[CH3:2])[CH2:31][C:32]1[CH:37]=[C:36]([F:38])[CH:35]=[C:34]([F:39])[CH:33]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 171741-(1H-Imidazol-1-yl)ethanoneHCID 57938831HCID 57938831, compound

Product 1

HCID 57938828HCID 57938828, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 1-acetylimidazole (0.035 g, 0.315 mmol) and triethylamine (0.04 mL, 0.286 mmol) to solution of 2-(R)-[2-(S)-amino-3-(3,5-difluorophenyl)-1-(S)-hydroxypropyl]-piperidine-1-carboxylic acid tert-butyl ester (0.106 mg, 0.286 mmol) in dichloromethane (10 mL) and stir 18 h at room temperature. Dilute with ethyl acetate and wash with 1 N hydrochloric acid (3×), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with dichloromethane and ethyl acetate) to give the title compound as a white solid (0.089 g, 76%).

Workup

  1. washwash with 1 N hydrochloric acid (3×), saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride
  2. dry with materialdry (magnesium sulfate)
  3. concentrationconcentrate
  4. custompurify
  5. wash(silica gel chromatography, eluting with dichloromethane and ethyl acetate)

Sources & evidence

ORD record
ord-d90cb5e2e3084d498fea6edc0690269b
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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