HCID 11628462, compound → HCID 11705399, compound

HRID 558025Notes

Reaction equation

HRID 558025 reaction equation
[C:1]([O:4][C@H:5]1[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@@H:23]([CH2:29][O:30][Si](C(C)(C)C)(C)C)[O:22][C@H:7]([O:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:6]1[N:38]=[N+:39]=[N-:40])(=[O:3])[CH3:2]>C1COCC1>[C:1]([O:4][C@H:5]1[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@@H:23]([CH2:29][OH:30])[O:22][C@H:7]([O:8][CH2:9][CH2:10][NH:11][C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[C@H:6]1[N:38]=[N+:39]=[N-:40])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 11628462HCID 11628462, compound

Product 1

HCID 11705399HCID 11705399, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 24 (575 mg, 0.99 mmol) in THF (5 mL), TREAT-HF (0.81 mL, 4.97 mmol) was added. The mixture was stirred under argon at rt overnight. Concentration and chromatography (2:1→0:1 toluene-EtOAc) gave 25 (448 mg, 0.96 μmmol, 97%); [α]D+60° (c 1.0, CHCl3); 13C NMR δ 20.7, 20.8 (CH3CO), 40.7 (HOCH2CH2NH), 61.4, 61.6, 66.4, 67.0, 67.5, 70.9, 71.0 (C-2-6, PhCH2O, OCH2CH2N), 98.2 (C-1), 128.3, 128.3, 128.7, 136.5 (aromatic C), 156.5 (NHCOOBn), 170.1, 170.5 (CH3CO); 1H NMR δ 2.04 (s, 3H), 2.1 (s, 3H), 3.32-3.46 (m, 2H), 3.54-3.60 (m, 2H), 3.62-3.78 (m, 3H), 4.02-4.04 (m, 1H), 5.06-5.18 (m, 3H), 5.22-5.28 (m, 1H), 5.36-5.40 (m, 1H), 7.28-7.38 (m, 5H); HRMS calcd for C20H26N4NaO9 [M+Na]+ 489.1597, found 489.1574.

Workup

  1. concentrationConcentration and chromatography (2:1→0:1 toluene-EtOAc)

Sources & evidence

ORD record
ord-06b708f660264120a9f4d9f4661956a2
Source dataset
uspto-grants-2011_11
Patent number
US08062641B2

Reaction notes

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