N-Iodosuccinimide → HCID 22999703, compound

HRID 397283Notes

Reaction equation

HRID 397283 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:12]=[C:11]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[O:10][N:9]=1)(=[O:3])[CH3:2].[I:27]N1C(=O)CCC1=O>O1CCCC1>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:27])=[C:11]([NH:13][S:14]([C:17]2[CH:18]=[CH:19][C:20]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][CH:22]=2)(=[O:15])=[O:16])[O:10][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 22999705HCID 22999705, compound

Product 1

HCID 22999703HCID 22999703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-3-isoxazolyl]oxy}ethyl acetate (Preparation 24) (1.17 g) in tetrahydrofuran (10 ml) was added N-iodosuccinimide (0.76 g). The reaction mixture was left stirring at room temperature overnight. The solvent was removed in vacuo to yield the crude material as a brown oil (1.5 g). The crude material was purified using the Biotage™ Flash 40i system (silica, 90 g) and eluted with hexane:ethyl acetate (1:9) to yield the product as a brown oil.

Workup

  1. waitThe reaction mixture was left
  2. customThe solvent was removed in vacuo
  3. customto yield the crude material as a brown oil (1.5 g)
  4. customThe crude material was purified
  5. washeluted with hexane:ethyl acetate (1:9)

Sources & evidence

ORD record
ord-0a7e05296c68470096999322e8eeed6b
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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