benzyl N-(E)-[1-oxo-2-(acetylthiomethyl)-3-(4-methoxylphenyl)propenyl]-beta-alaninate → N-(E)-[1-oxo-2-(mercaptomethyl)-3-(4-methoxyphenyl)propenyl]-beta-alanin
Reaction equation
[O:1]=[C:2]([NH:18][CH2:19][CH2:20][C:21]([O:23]CC1C=CC=CC=1)=[O:22])/[C:3](/[CH2:13][S:14]C(=O)C)=[CH:4]\[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1>CCOCC>[O:1]=[C:2]([NH:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])/[C:3](/[CH2:13][SH:14])=[CH:4]\[C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1Participants
3
Procedure
Saponification of the (E) diester obtained in Example 18 is carried out according to the experimental procedure described in Example 4. Yield: 69% (after flash chromatography, eluent: ether) m.p. 160° C. IR (nujol): 3340, 1730, 1620, 1580 cm-1 1H NMR (CDCl3): 9.10 (broad s, 1H); 7.75 and 7.15 (AB, 4H, J=8Hz); 6.60 (s, 1H); 6.15 (broad t, 1H): 3.75 (s, 3H); 3.50 to 3.45 (m, 4H); 2.50 (t, 2H, J=5 Hz): 1.70 (t; 1H, J=7 Hz). Microanalysis: C14H17O4NS Calc. % C=56.92 H=5.80 N=4.74 Found. % C=57.11 H=5.86 N=4.91
Sources & evidence
- ORD record
- ord-fe1432a76ae543d88068dd24eb91fbc7
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05612371
Reaction notes
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