Pyridine → HCID 22999712, compound

HRID 1935428Notes

Reaction equation

HRID 1935428 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 stirring solution of 2-{[5-({[4-(tert-butyl)phenyl]sulfonyl}amino)-4-iodo-3-isoxazolyl]oxy}ethyl acetate (Preparation 4) (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-338982eabc6640639445d54445b7c667
Source dataset
uspto-grants-2002_05
Patent number
US06387915B2

Reaction notes

Loading…