Hydrochloric Acid → HCID 20080104, compound
Reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].ClC(OCC(C)C)=O.[CH2:27]([NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([OH:37])[CH3:36])[CH3:28].Cl>C1COCC1.C(N(CC)CC)C>[CH2:27]([N:29]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH:35]([OH:37])[CH3:36])[C:15](=[O:17])[CH2:14][CH2:13][C:12](=[O:18])[C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=1)[CH3:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -8 °C
Procedure
A stirred solution of 4-((methanesulfonyl)amino)-γ-oxobenzenebutanoic acid (as described in EP 164 865) (0.49 g, 1.8 mmol) in THF (15 ml), under nitrogen, was treated with triethylamine (0.28 ml), cooled to -8° C. and treated during 5 minutes with isobutyl chloroformate (0.26 ml, 2.04 mmol). This mixture was kept at -5° to -8° C. for 90 minutes and then treated during 30 minutes with a solution of the product from Step III (0.31 g, 1.95 mmol) and triethyl amine (0.28 ml) in THF (10 ml). The mixture was kept at -8° C. for 2 hours and then poured into 1N HCl (19.2 ml). The product was extracted with EtOAc; the extract was washed successively with water, aqueous NaHCO3, water and brine; dried (MgSO4) and concentrated. The residue was crystallized frown EtOAc-hexane to give 0.36 g (48.6%) of N-ethyl-N-(6-hydroxyheptyl)-γ-oxo-4-((methanesulfonyl)amino)benzenebutanamide, mp 78°-80° C.
Workup
- waitThe mixture was kept at -8° C. for 2 hours
- extractionThe product was extracted with EtOAc
- washthe extract was washed successively with water, aqueous NaHCO3, water and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated
- customThe residue was crystallized frown EtOAc-hexane
Sources & evidence
- ORD record
- ord-bde43a882c7c4a27bdf3401323b28cd3
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05405997
Reaction notes
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