Hydrochloric Acid → HCID 18377664, compound

HRID 2301024Notes

Reaction equation

HRID 2301024 reaction equation
O.[OH-].[Li+].[Cl:4][C:5]1[CH:10]=[C:9]([S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:8]=[CH:7][C:6]=1[NH:24][C:25](=[O:33])[C:26]([O:29]C(=O)C)([CH3:28])[CH3:27].Cl.C(OCC)(=O)C>O.CO>[Cl:4][C:5]1[CH:10]=[C:9]([S:11]([C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21](=[O:23])[CH3:22])=[CH:18][CH:19]=2)(=[O:12])=[O:13])[CH:8]=[CH:7][C:6]=1[NH:24][C:25](=[O:33])[C:26]([OH:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 22287277HCID 22287277, compound

Product 1

HCID 18377664HCID 18377664, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of lithium hydroxide monohydrate (0.106 g) in water (1 ml) was added to a stirred solution of N-[2-chloro-4-(4-acetamidophenylsulphonyl)phenyl]-2-acetoxy-2-methylpropanamide (Method 16) (0.230 g) in methanol (2 ml) and the mixture was stirred at ambient temperature for 2 hours. Water (5 ml) was added and the solution was acidified to pH 2-3 with 1M hydrochloric acid. Ethyl acetate (20 ml) was added and the organic layer was washed with water (20 ml) and brine, then dried. Volatile material was removed by evaporation and the off-white solid was washed with ether to give the title compound (0.150 g) as a solid. NMR (CDCl3): 1.3 (s, 6H), 2.2 (s, 3H), 7.4 (s, 1 H), 7.7 (d, 2H), 7.8 (m, 3H), 7.9 (s, 1H), 8.7 (d, 1H), 9.6 (s, 1H); MS (ESP−): 409.

Workup

  1. washthe organic layer was washed with water (20 ml) and brine
  2. customdried
  3. customVolatile material was removed by evaporation
  4. washthe off-white solid was washed with ether

Sources & evidence

ORD record
ord-3bffccd351d94abdbc4fcc87685435a4
Source dataset
uspto-grants-2002_12
Patent number
US06498275B1

Reaction notes

Loading…