Hydrochloric Acid → 5-carboxymethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride
Reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13][CH2:12][CH:11]([NH:20][CH:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:22])[C:10]1=[O:28])=[O:7])(C)(C)C.[ClH:29]>O1CCOCC1>[ClH:29].[C:6]([CH2:8][N:9]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[S:13][CH2:12][CH:11]([NH:20][CH:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:22])[C:10]1=[O:28])([OH:7])=[O:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.9 g of the 5-t-butoxycarbonylmethyl-3-(1-ethoxycarbonylethylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one obtained in Example 11 was dissolved in 10 ml of a 6N solution of hydrogen chloride in dioxane and then reacted at room temperature for 30 minutes. After the reaction mixture was concentrated under reduced pressure, ether was added thereto so as to cause crystallization. The precipitated crystals were purified by silica gel column chromatography using a 50:3:5 mixture of chloroform, methanol and acetic acid as the eluent. Thus, there was obtained 400 mg of the desired compound.
Workup
- customreacted at room temperature for 30 minutes
- concentrationAfter the reaction mixture was concentrated under reduced pressure, ether
- additionwas added
- customcrystallization
- customThe precipitated crystals were purified by silica gel column chromatography
- additiona 50:3:5 mixture of chloroform, methanol and acetic acid as the eluent
Sources & evidence
- ORD record
- ord-2331d03625bd490c8f9b50bcf336b20d
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539150
Reaction notes
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