3-(1-ethoxycarbonylnonylamino)-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one → 5-carboxymethyl-3-(1-ethoxycarbonylnonylamino)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one
Reaction equation
[CH2:1]([O:3][C:4]([CH:6]([NH:15][CH:16]1[C:22](=[O:23])[N:21]([CH2:24][C:25]([O:27]C(C)(C)C)=[O:26])[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[S:18][CH2:17]1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5])[CH3:2]>Cl.O1CCOCC1>[C:25]([CH2:24][N:21]1[C:20]2[CH:32]=[CH:33][CH:34]=[CH:35][C:19]=2[S:18][CH2:17][CH:16]([NH:15][CH:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[C:22]1=[O:23])([OH:27])=[O:26]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
1.7 g of the 3-(1-ethoxycarbonylnonylamino)-5-t-butoxycarbonylmethyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one obtained in Example 17 was dissolved in 12 ml of a 6N solution of hydrogen chloride in dioxane and then reacted at room temperature for an hour. After this solution was concentrated under reduced pressure, 0.6 ml of triethylamine was added to the residue. This product was purified by silica gel column chromatography using a 5:2 mixture of benzene and acetic acid as the eluent. Thus, there was obtained 1.1 g of the desired compound in the form of a colorless, transparent oily material.
Workup
- customreacted at room temperature for an hour
- concentrationAfter this solution was concentrated under reduced pressure, 0.6 ml of triethylamine
- additionwas added to the residue
- customThis product was purified by silica gel column chromatography
- additiona 5:2 mixture of benzene and acetic acid as the eluent
Sources & evidence
- ORD record
- ord-a388d9c36ddd48019eee7dd60e7f2815
- Source dataset
- uspto-grants-1985_09
- Patent number
- US04539150
Reaction notes
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