Hcl-butanol → HCID 178451322, compound

HRID 1272441Notes

Reaction equation

HRID 1272441 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:11])[NH:9][OH:10])=[CH:4][C:3]=1[S:12]([NH:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30]([CH3:33])(=[O:32])=[O:31])=[CH:20][C:19]=1[O:34][CH2:35][C:36]([OH:38])=[O:37])(=[O:14])=[O:13].[CH2:39](O)[CH2:40][CH2:41][CH3:42].[ClH:44]>>[ClH:44].[CH2:39]([O:37][C:36](=[O:38])[CH2:35][O:34][C:19]1[CH:20]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[S:30]([CH3:33])(=[O:32])=[O:31])[CH:22]=[CH:23][C:18]=1[CH2:17][CH2:16][NH:15][S:12]([C:3]1[CH:4]=[C:5]([C:8](=[NH:11])[NH:9][OH:10])[CH:6]=[CH:7][C:2]=1[OH:1])(=[O:13])=[O:14])[CH2:40][CH2:41][CH3:42]

Participants

3

Reactant 2

HCID 22990708Hcl-butanolHCID 178504707HCID 178504707, compound

Product 1

HCID 178451322HCID 178451322, compound

Procedure

Method 2) A solution of 110 g of [4-[2-[2-hydroxy-5-(N-hydroxycarbamimidoyl)benzenesulfonylamino]ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetic acid in 1.00 L of 14% hydrogen chloride n-butanol solution was stirred at 100° C. for 2.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was washed with ethyl acetate to give 111 g of crude crystal. The crude crystal was recrystallized from n-butanol-diisopropyl ether to give 83.3 g of n-butyl[4-[2-[2-hydroxy-5-(N-hydroxycarbamimidoyl)benzenesulfonylamino]ethyl]-2′-methanesulfonylbiphenyl-3-yloxy]acetate hydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe residue was washed with ethyl acetate
  3. customto give 111 g of crude crystal
  4. customThe crude crystal was recrystallized from n-butanol-diisopropyl ether

Sources & evidence

ORD record
ord-e92b1eb145264b98952f80c62fd57986
Source dataset
uspto-grants-2007_04
Patent number
US07208524B2

Reaction notes

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