Diisopropylethylamine → HCID 86701331, compound

HRID 2283021Notes

Reaction equation

HRID 2283021 reaction equation
[NH2:1][C@H:2]1[CH2:10][O:9][CH2:8][C@H:7]([O:11][CH2:12][CH2:13][CH:14]([CH3:16])[CH3:15])[C@@H:6]([O:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C@H:5]([CH3:23])[O:4][C:3]1=[O:24].[OH:25][C:26]1[C:27]([C:34](O)=[O:35])=[N:28][CH:29]=[CH:30][C:31]=1[O:32][CH3:33].C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>C(Cl)Cl>[CH2:12]([O:11][C@@H:7]1[C@@H:6]([O:17][CH2:18][CH2:19][CH:20]([CH3:22])[CH3:21])[C@H:5]([CH3:23])[O:4][C:3](=[O:24])[C@@H:2]([NH:1][C:34](=[O:35])[C:27]2[C:26]([OH:25])=[C:31]([O:32][CH3:33])[CH:30]=[CH:29][N:28]=2)[CH2:10][O:9][CH2:8]1)[CH2:13][CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 110411213-Hydroxy-4-methoxypyridine-2-carboxylic acidHCID 86701332HCID 86701332, compound

Product 1

HCID 86701331HCID 86701331, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3S,7S,8S,9S)-3-amino-7,8-bis(isopentyloxy)-9-methyl-1,5-dioxonan-2-one (130 mg, 0.376 mmol) and 3-hydroxy-4-methoxypicolinic acid (70.0 mg, 0.414 mmol) were diluted with DCM (3763 μl). PyBOP (215 mg, 0.414 mmol) was added, followed by N-ethyl-N-isopropylpropan-2-amine (216 μl, 1.242 mmol), and the mixture was stirred at room temperature until thin layer chromatography (TLC) indicated complete consumption of starting material. The reaction mixture was purified by column chromatography (SiO2; hexanes/EtOAc) to furnish the title compound (79.1 mg, 0.159 mmol, 42.3% yield) as a white solid: mp 61-70° C.; IR (thin film) 3530, 3371, 2955, 2873, 1750, 1649, 1529, 1262 cm−1; 1H NMR (400 MHz, CDCl3) δ 11.94 (s, 1H), 8.67 (d, J=8.1 Hz, 1H), 8.01-7.98 (m, 1H), 6.87 (d, J=5.2 Hz, 1H), 5.04 (ddd, J=8.2, 6.8, 5.0 Hz, 1H), 5.01-4.89 (m, 1H), 4.05 (dd, J=11.9, 6.8 Hz, 1H), 3.94 (s, 3H), 3.92-3.85 (m, 1H), 3.85-3.78 (m, 2H), 3.66-3.58 (m, 2H), 3.57-3.48 (m, 2H), 3.26-3.14 (m, 2H), 1.69 (dp, J=13.4, 6.7 Hz, 2H), 1.51-1.38 (m, 7H), 0.90 (dt, J=6.2, 2.7 Hz, 12H); 13C NMR (101 MHz, CDCl3) δ 170.30, 168.94, 155.32, 148.72, 140.66, 130.22, 109.56, 85.02, 83.63, 75.28, 73.94, 73.17, 72.48, 69.35, 56.09, 52.12, 39.23, 38.95, 24.96, 22.91, 22.67, 22.62, 22.50, 18.59; HRMS-ESI (m/z) [M+Na]+ calcd for C25H40N2NaO8, 519.2677, found 519.2687.

Workup

  1. customconsumption of starting material
  2. customThe reaction mixture was purified by column chromatography (SiO2; hexanes/EtOAc)

Sources & evidence

ORD record
ord-3118a7f62c52451dacfeedb9c68a578a
Source dataset
uspto-grants-2015_09
Patent number
US09144239B2

Reaction notes

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