Pyridine → HCID 22999712, compound

HRID 397282Notes

Reaction equation

HRID 397282 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[O:10][N:9]=1)(=[O:3])[CH3:2].N1[CH:33]=[CH:32][CH:31]=CC=1>ClCCl>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[C:12]([I:13])=[C:11]([N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])=[CH:22][CH:23]=2)(=[O:17])=[O:16])[C:1]([O:4][CH2:5][CH:32]([CH3:31])[CH3:33])=[O:3])[O:10][N:9]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 1049PyridineHCID 22999703HCID 22999703, compound

Product 1

HCID 22999712HCID 22999712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a string solution of 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-3-isoxazolyl]oxy}ethyl acetate (Preparation 23) (9.44 g) in dichloromethane was added pyridine (1.65 ml) followed by the slow addition of isobutylchloroforomate (2.41 ml) over 10 minutes. The reaction mixture was stirred at room temperature for one hour. The solvent was removed in vacuo to yield the crude material. This was purified using column chromatography (300 g silica, compound loaded with dichloromethane (15 ml)) using a gradient elution of hexane (100% to 75%) and ethyl acetate (0% to 25%) to yield the desired compound as a yellow oil (7.70 g).

Workup

  1. additionfollowed by the slow addition of isobutylchloroforomate (2.41 ml) over 10 minutes
  2. customThe solvent was removed in vacuo
  3. customto yield the crude material
  4. customThis was purified
  5. washa gradient elution of hexane (100% to 75%) and ethyl acetate (0% to 25%)

Sources & evidence

ORD record
ord-49796d8d12364fea9e9ef1ab49fd8fb1
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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