1-Hydroxybenzotriazole → (2S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)hexanamide

HRID 1643273Notes

Reaction equation

HRID 1643273 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][NH2:8].C1C=CC2N(O)N=NC=2C=1.C([O-])(O)=O.[Na+].[F:24][C:25]1[CH:30]=[CH:29][C:28]([C@H:31]([O:41][CH3:42])[CH2:32][C@H:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34](O)=[O:35])=[CH:27][CH:26]=1.CCN=C=NCCCN(C)C.Cl>C(Cl)Cl>[F:24][C:25]1[CH:26]=[CH:27][C:28]([C@H:31]([O:41][CH3:42])[CH2:32][C@H:33]([CH2:37][CH2:38][CH2:39][CH3:40])[C:34]([NH:8][O:7][CH:2]2[CH2:3][CH2:4][CH2:5][CH2:6][O:1]2)=[O:35])=[CH:29][CH:30]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 59568810(S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hexanoic acid

Product 1

HCID 59568840(2S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)hexanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of O-(tetrahydro-2H-pyran-2-yl)hydroxylamine (73.8 mg, 0.63 mmol), HOBT (340 mg, 2.5 mmol), NaHCO3 (423 mg, 2.9 mmol), and the (S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)hexanoic acid in 30 mL DCM was added EDC.HCl (407 mg, 2.1 mmol) as solid. The reaction mixture was stirred for 3 h at room temperature and then the solvent was removed under reduced pressure. The product was isolated by flash column chromatography, eluting with 10% to 60% EtOAc/Hexane gradient solvent to give 128 mg of the title compound.

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe product was isolated by flash column chromatography
  3. washeluting with 10% to 60% EtOAc/Hexane gradient solvent

Sources & evidence

ORD record
ord-5186afcda77b4e9d84ddf5d34eec2a2a
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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