Tetrahydrofuran → HCID 86652366, compound

HRID 2272819Notes

Reaction equation

O[C@@H:2]1[C@H:7](O)[C@@H](OC)C(C)(C)O[C@H:3]1[O:13][C:14]1[C:23]([CH3:24])=[C:22]2[C:17]([CH:18]=[C:19]([NH:26]S(C3C=CC=CC=3)(=O)=O)[C:20](=[O:25])[O:21]2)=[CH:16][CH:15]=1.OC1C(C)=C2C(C=C(N[C:50](=[O:59])[O:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)C(=O)O2)=CC=1.C1(P([C:73]2[CH:78]=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(O[C:83](/[N:85]=N/C(OC(C)C)=O)=O)C.C1[CH2:97][O:96]CC1>>[CH3:24][C:23]1[C:14]([O:13][CH:3]2[CH2:2][CH2:7][N:85]([CH3:83])[CH2:78][CH2:73]2)=[CH:15][CH:16]=[C:17]2[C:22]=1[O:21][C:20](=[O:25])[C:19]([NH:26][C:97](=[O:96])[C:50]([O:51][CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:59])=[CH:18]2

Participants

Reactant 5

HCID 8028Tetrahydrofuran

HCID 11776Triphenylphosphine

HCID 5363146Diisopropyl azodicarboxylate

HCID 10782279HCID 10782279, compound

HCID 24850965HCID 24850965, compound

Product 1

HCID 86652366HCID 86652366, compoundYield 63%

Procedure

General procedure II for Mitsunobu coupling: To a solution of 21 (0.64 g, 5.59 mmol), 7 (1.74 g, 5.59 mmol) and triphenylphosphine (2.93 g, 11.2 mmol) in THF (50 mL) was added diisopropylazodicarboxylate (2.26 g, 11.2 mmol) dropwise. The reaction mixture was stirred at room temperature for 4 hours and concentrated under vacuum. The residue was purified by column chromatography on silica using methylene chloride and methanol (10:1) as eluent to afford 28a as colorless foam (1.48 g, 63%). 1H MNR (400 MHz, CDCl3) δ 8.28 (s, 1H), 7.55 (s, 1H), 7.45˜7.38 (m, 5H), 7.29 (d, J=8.0, 1H), 6.87 (d, J=8.0, 1H), 5.25 (s, 2H), 4.49 (m, 1H), 2.72˜2.68 (m, 2H), 2.52˜2.49 (m, 2H), 2.38 (s. 3H), 2.35 (s, 1H), 2.11˜2.05 (m, 2H), 1.96˜1.92 (m, 2H). 13C MNR (100 MHz, CDCl3) δ 159.1, 156.8, 153.4, 149.4, 135.8, 128.9, 128.7, 128.4, 125.3, 122.5, 121.6, 115.4, 113.5, 110.7, 77.4, 67.6, 52.4, 46.4, 30.8, 8.6. IR (film) νmax 3406, 3319, 2939, 2849, 2791, 1711, 1609, 1524, 1366, 1271, 1227, 1204, 1103, 1038, 1024 cm−1. HRMS (ESI+) m/z Calc for [M+H+] C24H27N2O5 423.1920. found 423.1920.

Workup

concentrationconcentrated under vacuum
customThe residue was purified by column chromatography on silica

Sources & evidence

ORD record: ord-daefabdf708b483994e7bbc42a25c9bb
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09120774B2

Reaction notes

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