O-chloroacetylcarbamoyl fumagillol → Fumagillol

HRID 486129Notes

Reaction equation

HRID 486129 reaction equation
[CH3:1][C:2]([CH3:27])=[CH:3][CH2:4][C@@H:5]1[O:7][C@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([O:17]C(NC(CCl)=O)=O)[C@H:10]1[O:25][CH3:26])[CH3:8].[N+]1([O-])C=CC=CC=1.[Na].COC1C=CC(C(C2C(=O)NC(=S)N(C3C=CC(Cl)=CC=3)C=2[O-])C2C(=O)NC(=S)N(C3C=CC(Cl)=CC=3)C=2O)=CC=1C[NH+]1C(C2C=CC=NC=2)CCCC1>>[CH3:1][C:2]([CH3:27])=[CH:3][CH2:4][C@H:5]1[O:7][C@@:6]1([C@@H:9]1[C@:14]2([O:16][CH2:15]2)[CH2:13][CH2:12][C@@H:11]([OH:17])[C@H:10]1[O:25][CH3:26])[CH3:8]

Participants

3

Reactant 2

HCID 14942883O-chloroacetylcarbamoyl fumagillolHCID 131718341sodium pyridine-N-oxide 2-thiolate

Product 1

HCID 222778FumagillolYield 148.3%

Procedure

In the same manner as in Example 42, O-chloroacetylcarbamoylfumagillol (144 mg) was reacted with sodium pyridine-N-oxide-2-thiolate (60 mg) with stirring at room temperature for 10 minutes. Purification by silica gel column chromatography (eluent: chloroform-methanol=20:1) gave colorless, powdery O-C(pyridine-N-oxide-2-yl)thioacetylcarbamoyl]fumagillol (150 mg) (85% yield). 1H-NMR (CDCl3) δ: 1.07 (1H, m), 1.21 (3H, s), 1.65 (3H, s), 1.74 (3H, s), 1.8-2.4 (EH, m), 2.55 (1H, d, J=4.4 Hz), 2.57 (1H, t, J=6.4 Hz), 2.98 (1H, d, J=4.4 Hz), 3.46 (3H, s), 3.68 (1H, dd, J=11.4 Hz, J=2.6 Hz), 3.94 (1H, d, J=15.4 Hz), 4.13 (1H, d, J=15.4 Hz), 5.19 (1H, m), 5.60 (1H, m), 7.1-7.35 (2H, m), 7.50 (1H, d, J=7.2 Hz), 8.33 (1H, d, J=6.2 Hz), 9.29 (1H, br s).

Workup

  1. customPurification by silica gel column chromatography (eluent: chloroform-methanol=20:1)
  2. customgave colorless

Sources & evidence

ORD record
ord-5e63e56b1b904b9a934f95842c343312
Source dataset
uspto-grants-1994_03
Patent number
US05290807

Reaction notes

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