Diisopropylethylamine → HCID 117974483, compound

HRID 1776116Notes

Reaction equation

HRID 1776116 reaction equation
[Cl-].[CH3:2][C@@H:3]1[O:11][C:10](=[O:12])[C@@H:9]([NH3+:13])[CH2:8][CH2:7][CH2:6][C@H:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C@H:4]1[O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[OH:29][C:30]1[C:31]([C:38](O)=[O:39])=[N:32][CH:33]=[CH:34][C:35]=1[O:36][CH3:37].C(N(CC)C(C)C)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[OH:29][C:30]1[C:31]([C:38]([NH:13][C@H:9]2[CH2:8][CH2:7][CH2:6][C@H:5]([CH2:14][C:15]3[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=3)[C@@H:4]([O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C@H:3]([CH3:2])[O:11][C:10]2=[O:12])=[O:39])=[N:32][CH:33]=[CH:34][C:35]=1[O:36][CH3:37]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 110411213-Hydroxy-4-methoxypyridine-2-carboxylic acidHCID 117974129HCID 117974129, compound

Product 1

HCID 117974483HCID 117974483, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL screw top vial was charged with (3S,7R,8R,9S)-9-methyl-7-(4-methylbenzyl)-2-oxo-8-phenoxyoxonan-3-aminium chloride (259 mg, 0.642 mmol), 3-hydroxy-4-methoxypicolinic acid (122 mg, 0.721 mmol), anhydrous CH2Cl2 (6.5 mL), and N,N-diisopropylethylamine (340 μL, 1.95 mmol). To the mixture was added PyBOP (376 mg, 0.723 mmol) and the reaction was stirred at room temperature for 1.5 h and then directly purified by column chromatography on SiO2 (2→30% acetone/hexanes) to provide the title compound as a white solid (162 mg, 49%): mp 62-66° C.; 1H NMR (400 MHz, CDCl3) δ 12.09 (s, 1H), 8.48 (d, J=8.2 Hz, 1H), 7.98 (d, J=5.1 Hz, 1H), 7.37-7.28 (m, 2H), 7.12-6.93 (m, 7H), 6.86 (d, J=5.2 Hz, 1H), 5.14 (dq, J=9.2, 6.4 Hz, 1H), 4.62 (dt, J=10.9, 7.4 Hz, 1H), 4.35 (t, J=8.9 Hz, 1H), 3.93 (s, 3H), 2.99 (dd, J=13.3, 3.2 Hz, 1H), 2.42-2.26 (m, 5H), 2.16-2.04 (m, 1H), 1.79-1.52 (m, 3H), 1.41-1.23 (m, 4H), 1.08-0.98 (m, 1H); 13C NMR (101 MHz, CDCl3) δ 172.06, 168.59, 159.58, 155.27, 148.66, 140.47, 136.92, 135.38, 130.28, 129.63, 128.98, 128.59, 121.16, 115.48, 109.43, 81.02, 74.89, 55.99, 51.43, 45.59, 36.34, 33.47, 26.57, 20.95, 18.78, 18.33; ESIMS: m/z 519 ([M+H]+).

Workup

  1. customdirectly purified by column chromatography on SiO2 (2→30% acetone/hexanes)

Sources & evidence

ORD record
ord-270563b67f6c40de87a365f3dff318c7
Source dataset
uspto-grants-2016_02
Patent number
US09265253B2

Reaction notes

Loading…