Chloroform → HCID 86750531, compound
Reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[C@@H:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][S:7][C@H:6]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:4].[CH3:23][C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1.C(Cl)(Cl)Cl>C1CCCCC1>[CH3:23][C:24]1[CH:25]=[C:26]([NH:30][C:31](=[O:32])[NH:1][CH2:2][C:3]([N:5]2[C@@H:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][S:7][C@H:6]2[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:4])[CH:27]=[CH:28][CH:29]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The operation is carried out in a fashion similar to that described in Example 34, but starting from 0.3 g of tert-butyl (2S,4S)-3-(2 aminoacetyl)-2-phenyl-4-thiazolidinecarboxylate and 0.12 cm3 of 3-methylphenyl isocyanate. After vigorous stirring in cyclohexane, 0.16 g of tert-butyl (2S,4S)-3-{2-[3-(3-methylphenyl)ureido]acetyl}-2-phenyl-4-thiazolidinecarboxylate is thus obtained in the form of an amorphous pale yellow powder ([α]D20 =-62.0°±1.1° (C=1.02%; CHCl3)). [Proton NMR (250 MHz, DMSO D6, δ in ppm), 2 rotamers at room temperature, peak coalescence at 120° C., general description valid for the other products of the thiazolidine family (at 120° C.): 1.50 (bs, 9H, (CH3)3); 2.3 (s, 3H, CH3); 3.25 and 3.5 (ABX, 2H, CH2S); 3.7 and 4.05 (ABX, 2H, CH2N); 5.0 (bd, 1H, CHN); 6.2 (bds, 1H, NH); 6.4 (bs, 1H, SCHN); 6.7 (bd, 1H, N--C6H4 --C in position 4 or 6); 7.05 to 7.2 (m, 3H, N--C6H4 --C in position 2, 4 and 5); 7.35 (m, 3H, C6H5); (bd, 2H, C6H5); 8.35 (bs, 1H, NH). Infrared spectrum (KBr), characteristic bands in cm-1 : 3380, 2990, 2940, 2860, 1745, 1650, 1615, 1600, 1560, 1495, 1460, 1375, 1155, 785, 735, 700].
Sources & evidence
- ORD record
- ord-dffc044ff54d44268d218f69d36ff311
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610144
Reaction notes
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