Piperidine → 5-[4-hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-2-phenyl-3H-pyran-2-yl]pentanoic acid

HRID 357856Notes

Reaction equation

HRID 357856 reaction equation
Br[C:2]1[C:7](=[O:8])[O:6][C:5]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][C:3]=1[OH:22].[CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32])([CH3:25])[CH3:24].N1CCCCC1>ClCCl>[OH:22][C:3]1[CH2:4][C:5]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:6][C:7](=[O:8])[C:2]=1[S:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH:23]([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 96003Benzenethiol, 2-(1-methylethyl)-HCID 547215845-[5-Bromo-4-hydroxy-6-oxo-2-phenyl-3,6-dihydro-2H-pyran-2-yl]pentanoic acid

Product 1

HCID 547200215-[4-hydroxy-5-(2-isopropylphenyl)sulfanyl-6-oxo-2-phenyl-3H-pyran-2-yl]pentanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.1 mmol of 5-[5-bromo-3,6-dihydro-4-hydroxy-6-oxo-2-phenyl-2H-pyran-2-yl]pentanoic acid (prepared in example DDD), 1.3 mmol of 2-isopropylbenzenethiol, and 1.3 mmol of piperidine in 20 mL of dichloromethane. The crude product was chromatographed on silica gel, eluting first with 5% methanol in chloroform and then with 9:1:0.5 chloroform:methanol:acetic acid, to give the title compound, (m.p. 145°-146° C.). 1H NMR (DMSO-d6) δ 1.07-1.19 (t plus m, 7 H), 1.25 (m, 1 H), 1.43 (m, 2 H), 1.91 (m, 2 H), 2.15 (t, 2 H), 3.19 (m, 1 H), 3.41 (2 H+H2O), 5.81 (d, 1 H), 6.54 (t, 1 H), 6.93 (t, 1 H), 7.12 (d, 1 H), 7.29-7.44 (m, 5 H).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel
  3. washeluting first with 5% methanol in chloroform

Sources & evidence

ORD record
ord-0128d827fd0843598c2cb21f22eeca7d
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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