Pyridine → HCID 58877664, compound

HRID 2118221Notes

Reaction equation

HRID 2118221 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[CH:20][CH:19]=2)=[C:9](\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH2:10][CH3:11])=[CH:4][CH:3]=1.Cl[C:34]([O:36][C:37]1[CH:42]=[CH:41][C:40]([N+:43]([O-:45])=[O:44])=[CH:39][CH:38]=1)=[O:35].N1C=CC=CC=1>C(Cl)Cl>[N+:43]([C:40]1[CH:41]=[CH:42][C:37]([O:36][C:34]([O:1][C:2]2[CH:7]=[CH:6][C:5](/[C:8](/[C:18]3[CH:19]=[CH:20][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])=[CH:22][CH:23]=3)=[C:9](\[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)/[CH2:10][CH3:11])=[CH:4][CH:3]=2)=[O:35])=[CH:38][CH:39]=1)([O-:45])=[O:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 58877662HCID 58877662, compound

Product 1

HCID 58877664HCID 58877664, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 12 (0.5 g, 1.17 mmol, ˜9:1 Z/E ratio by 1HNMR) in CH2Cl2 (10 mL) was added p-nitrophenyl chloroformate (0.35 g, 1.76 mmol) and pyridine (0.29 mL, 0.28 g, 3.58 mmol). The reaction mixture was stirred at ambient temperature for 18 h and then concentrated. The residue was purified by chromatography (silica gel, hexanes/EtOAc, 8:1) to provide 38 (0.63 g, 91%, ˜9:1 Z/E mixture) as a cream-colored solid foam. 1HNMR (400 MHz, DMSO-d6): δ 0.85 (t, J=7.4 Hz, 3H), 1.42 (s, 9H), 2.39 (q, J=7.4 Hz, 2H), 6.50 (d, J=16 Hz, 1H), 6.92 (d, J=8.6 Hz, 2H), 7.1-7.8 (m, 14H), 8.3-8.4 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (silica gel, hexanes/EtOAc, 8:1)

Sources & evidence

ORD record
ord-3da22e0a1ae947459cb3dadf58ec3c5d
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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