O-chloroacetylcarbamoyl fumagillol → Fumagillol

HRID 1940037Notes

Reaction equation

HRID 1940037 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].[Na].CN(C)CCN1C(S)=NN=N1>>[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 178483734HCID 178483734, compound

Product 1

HCID 222778FumagillolYield 158.4%

Procedure

In the same manner as in Example 42, O-chloroacetylcarbamoylfumagillol (195 mg) was reacted with 1-(2-dimethylaminoethyl)-5-mercaptotetrazole sodium (113 mg) with stirring at room temperature for 1 hour. Purification by silica gel column chromatography (eluent: ethyl acetate) gave colorless, powdery O-[[1-(2-dimethylaminoethyl)tetrazol]-5-yl)thioacetylcarbamoyl]fumagillol (217 mg) (83% yield).

Workup

  1. customPurification by silica gel column chromatography (eluent: ethyl acetate)
  2. customgave colorless

Sources & evidence

ORD record
ord-b79d48a4ceb64144b11c35448621a62d
Source dataset
uspto-grants-1997_12
Patent number
US05698586

Reaction notes

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