Triethylamine → N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamide

HRID 1487511Notes

Reaction equation

HRID 1487511 reaction equation
[NH2:1][C@@H:2]([CH2:14][F:15])[C@@H:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[N+:12]=[N-:13])=[CH:7][CH:6]=1)[OH:4].C(N(CC)CC)C.[Cl:23][CH:24]([Cl:30])[C:25](OCC)=[O:26]>CO>[N:11]([C:8]1[CH:7]=[CH:6][C:5]([C@@H:3]([OH:4])[C@H:2]([NH:1][C:25](=[O:26])[CH:24]([Cl:30])[Cl:23])[CH2:14][F:15])=[CH:10][CH:9]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10808Ethyl dichloroacetateHCID 86695457(1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol

Product 1

HCID 86695459N-[(1S,2R)-2-(4-Azido-phenyl)-1-fluoromethyl-2-hydroxy-ethyl]-2,2-dichloro-acetamideYield 16.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the stirred solution of (1R,2R)-2-Amino-1-(4-azido-phenyl)-3-fluoro-propan-1-ol (600 mg, 2.83 mmol) in methanol (6.5 mL) is added triethyl amine (0.57 g, 5.64 mmol) and ethyl dichloroacetate (0.88 g, 5.60 mmol). Resulting reaction mixture is stirred under nitrogen at room temperature for 16 hours. Solvent is evaporated in vacuo to get the crude material purified by column chromatography eluting in 0.5% methanol in dichloromethane to afford the title compound (150 mg). 1H-NMR (400 MHz, DMSO-d6) δ: 4.40-4.41 (m, 1H), 4.24-4.26 (m, 0.5H), 4.36-4.38 (m, 0.5H), 4.52-4.54 (m, 0.5H), 4.64-4.66 (m, 0.5H), 4.84 (t, 1H, J=3.64 Hz), 5.96 (d, 1H, J=4.24 Hz), 6.49 (s, 1H), 7.05 (d, 2H, J=8.48 Hz), 7.38 (d, 2H, J=8.44 Hz), 8.58 (d, 1H, J=8.98 Hz). LC-Ms (m/z): [M−H]=318.8.

Workup

  1. customResulting
  2. customreaction mixture
  3. customSolvent is evaporated in vacuo
  4. customto get the crude material
  5. custompurified by column chromatography
  6. washeluting in 0.5% methanol in dichloromethane

Sources & evidence

ORD record
ord-23b09559ce87434da68c086f30c3ad0b
Source dataset
uspto-grants-2016_08
Patent number
US09428528B2

Reaction notes

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