HCID 10349179, compound → HCID 10077492, compound
Reaction equation
[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:16]([C:17]([O:19]CC)=[O:18])=[C:15]([CH:22]4[CH2:24][CH2:23]4)[N:14]=[C:13]3[CH2:25][CH3:26])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][S:34]([C:37]([F:40])([F:39])[F:38])(=[O:36])=[O:35]>CO.[OH-].[Na+].[Cl-].[Na+].O.O>[Br:1][C:2]1[C:6]2[CH:7]=[C:8]([CH2:11][N:12]3[C:16]([C:17]([OH:19])=[O:18])=[C:15]([CH:22]4[CH2:23][CH2:24]4)[N:14]=[C:13]3[CH2:25][CH3:26])[CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[NH:33][S:34]([C:37]([F:40])([F:38])[F:39])(=[O:36])=[O:35]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A mixture of the product of Example 3 (1.72 g) and 2N aqueous sodium hydroxide (15 ml) in methanol (30 ml) was stirred at room temperature for 6 h. After standing overnight, the solution was diluted with further 2N aqueous sodium hydroxide (10 ml), stirred for a further 2 h at room temperature and then heated at 40° for 90 mins. After cooling, the solution was diluted with brine (80 ml) and water (50 ml) before being washed with ether (100 ml). The aqueous phase was then acidified with 2N hydrochloric acid to pH 1 and the cloudy solution was extracted with ethyl acetate (3×90 ml). The combined ethyl acetate extracts were dried and concentrated in vacuo to afford the title compound (1.72 g) as an off-white foam.
Workup
- waitAfter standing overnight
- stirringstirred for a further 2 h at room temperature
- temperatureheated at 40° for 90 mins
- temperatureAfter cooling
- washbefore being washed with ether (100 ml)
- extractionthe cloudy solution was extracted with ethyl acetate (3×90 ml)
- dry with materialThe combined ethyl acetate extracts were dried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-937b6efac1134e589ca974b5f42ace41
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05332831
Reaction notes
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