Sodium Hydroxide → HCID 53691393, compound
Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH:11]1[C:17]2=[C:18]3[C:23](=[N:24][C:25]4[CH2:26][CH2:27][CH2:28][CH:15]([C:16]=42)[S:14][CH2:13][C:12]1=O)[CH:22]=[CH:21][CH:20]=[CH:19]3.[OH-].[Na+]>O1CCCC1>[NH:11]1[C:17]2=[C:18]3[C:23](=[N:24][C:25]4[CH2:26][CH2:27][CH2:28][CH:15]([C:16]=42)[S:14][CH2:13][CH2:12]1)[CH:22]=[CH:21][CH:20]=[CH:19]3Participants
Procedure
To a solution of lithium aluminum hydride (30 ml of a 1M solution in tetrahydrofuran diluted to 130 ml with tetrahydrofuran) was added aluminum chloride (3.94 g). The mixture was stirred for 30 mins and then 1,3,4a,5,6,7-hexahydro-2H-quino[4,3,2-ef][1,4]benzthiazepin-2-one (6.65 g) was added. The reaction mixture was stirred for 1 hr and then poured into 60 ml of 10% sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate and the combined organic extracts were washed with water, saturated sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was preadsorbed on silica and purified by flash chromatography (2% triethylamine/ethyl acetate) to give 3.0 g (48%) of product, mp 171°-175° C. Recrystallization from methanol/water gave the analytical sample, mp 175°-177° C.
Workup
- stirringThe reaction mixture was stirred for 1 hr
- extractionThe aqueous phase was extracted with ethyl acetate
- washthe combined organic extracts were washed with water, saturated sodium chloride
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- custompurified by flash chromatography (2% triethylamine/ethyl acetate)
Sources & evidence
- ORD record
- ord-e36e2343db3c4be68be1d857c03f2f88
- Source dataset
- uspto-grants-1991_02
- Patent number
- US04994452
Reaction notes
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