Acetic Anhydride → N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-{alpha-acetoxy-2-[2-(acetoxy)ethyl]-4,5-(methylenedioxy)benzyl}thieno[2,3-b]-pyridine-3-sulfonamide

HRID 2269005Notes

Reaction equation

HRID 2269005 reaction equation
[Cl:1][C:2]1[C:3]([CH3:40])=[N:4][O:5][C:6]=1[N:7]([CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20]([OH:33])[C:21]1[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[CH2:30][CH2:31][OH:32])(=[O:10])=[O:9].[C:41](OC(=O)C)(=[O:43])[CH3:42].[CH3:48][CH2:49][O:50]C(C)=O>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([CH3:40])=[N:4][O:5][C:6]=1[N:7]([CH2:34][O:35][CH2:36][CH2:37][O:38][CH3:39])[S:8]([C:11]1[C:19]2[C:14](=[N:15][CH:16]=[CH:17][CH:18]=2)[S:13][C:12]=1[CH:20]([O:33][C:49](=[O:50])[CH3:48])[C:21]1[CH:26]=[C:25]2[O:27][CH2:28][O:29][C:24]2=[CH:23][C:22]=1[CH2:30][CH2:31][O:32][C:41](=[O:43])[CH3:42])(=[O:9])=[O:10]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 57235804N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-[alpha-hydroxy-2-(2-hydroxyethyl)-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide

Product 1

HCID 18614042N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyethoxymethyl)-2-{alpha-acetoxy-2-[2-(acetoxy)ethyl]-4,5-(methylenedioxy)benzyl}thieno[2,3-b]-pyridine-3-sulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(4-chloro-3-methyl-5-isoxazolyl)-N-(methoxyeth-oxymethyl)-2-[α-hydroxy-2-(2-hydroxyethyl)-4,5-(methylenedioxy)benzyl]thieno[2,3-b]pyridine-3-sulfonamide (0.11 g, 0.19 mmoles) in pyridine (2 ml) was added acetic anhydride (0.18 ml, 1.9 mmoles). The reaction solution was stirred 2 hours at ambient temperature, then diluted with EtOAc (50 ml) and washed with 2% HCl (2×100 ml). The organic layer was dried (MgSO4), filtered and concentrated to collect 0.13 g (100%) of the title compound as a yellow oil.

Workup

  1. washwashed with 2% HCl (2×100 ml)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto collect 0.13 g (100%) of the title compound as a yellow oil

Sources & evidence

ORD record
ord-2fc3a6fd701b44c28ea05fe13a3d00e4
Source dataset
uspto-grants-2001_12
Patent number
US06329387B2

Reaction notes

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