Hydrochloric Acid → N-[2-(3-Acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]-2-chloroacetamide
Reaction equation
[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]([OH:22])[CH2:13][NH:14][C:15](=O)[O:16]C(C)(C)C)[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2].Cl.C(N(CC)CC)C.[Cl:33][CH2:34]C(Cl)=O>O1CCOCC1.C(Cl)Cl>[C:1]([C:4]1[C:5]([O:23][CH3:24])=[C:6]([CH:12]([OH:22])[CH2:13][NH:14][C:15](=[O:16])[CH2:34][Cl:33])[C:7]([CH3:11])=[C:8]([Cl:10])[CH:9]=1)(=[O:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
tert-Butyl [2-(3-acetyl-5-chloro-2-methoxy-6-methylphenyl)-2-hydroxyethyl]carbamate (170 mg, 0.47 mmol) (Peak 1 from step 2) was treated with 4.0 M hydrogen chloride in 1,4-dioxane (12 mL) for 15 minutes. The solvents were evaporated, methylene chloride (6 mL) and triethylamine (200 μL, 1.4 mmol) were added and the mixture cooled to 0° C. Chloroacetyl chloride (45 μL, 0.56 mmol) was added slowly and was stirred for 10 minutes at 0° C. The solvents were evaporated to dryness. Water was added and the mixture was extracted with ethyl acetate. The combined extracts were washed with brine, dried over sodium sulfate, and concentrated to give the crude residue as a single enantiomer. LCMS calculated for C14H17Cl2NO4Na (M+Na)+: m/z=356.1; found: 356.1.
Workup
- customThe solvents were evaporated
- customThe solvents were evaporated to dryness
- additionWater was added
- extractionthe mixture was extracted with ethyl acetate
- washThe combined extracts were washed with brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-657d077639f34eb99ff67216513d4325
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09199982B2
Reaction notes
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