(S)-N-[2-[2-(R)-(1,1-dimethylethyloxycarbonylamino)-3-phenylpropionyloxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate → (+)-N-[2-hydroxyl-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate
Reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].CC(C)(OC(N[C@H](CC1C=CC=CC=1)C([O:19][C@@H:20]([CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:21][O:22][N:23]=[C:24]([Cl:31])[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)=O)=O)C>CO>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]\[C:4]([OH:6])=[O:5].[OH:19][CH:20]([CH2:32][N:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:21][O:22][N:23]=[C:24]([Cl:31])[C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
2.16 g (3.26 mmole) of (S)—N-[2-[2-(R)-(1,1-dimethylethyloxycarbonylamino)-3-phenylpropionyloxy]-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride (Z)-2-butenedioate (1:1) (see Example 18) was suspended in 40 ml of methanol and boiled for 1 hour, then evaporated to dryness. The residue was triturated with 20 ml of ethyl acetate, the precipitate was filtered, washed with ethyl acetate. This crude product was recrystallized in isopropyl alcohol to yield the title compound.