Formaldehyde → ethyl (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamate
Reaction equation
[NH2:1][CH2:2][C:3]([N:5]1[CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH:6]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[O:4].[CH2:23]=[O:24].[K+].[Br-].[NH2:27][C:28]1[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=1)/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34]>ClCCCl>[C:10]([O:9][C:7]([CH:6]1[CH2:14][CH2:15][CH:16]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:5]1[C:3](=[O:4])[CH2:2][NH:1][C:23](=[O:24])[NH:27][C:28]1[CH:29]=[C:30]([CH:38]=[CH:39][CH:40]=1)/[CH:31]=[CH:32]/[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:8])([CH3:13])([CH3:12])[CH3:11]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
By proceeding in a fashion similar to that described in Example 3, but starting from 3.6 g of N,N'-carbonyldiimidazole, 6.2 g of tert-butyl (2RS,5SR)-1-(2-aminoacetyl)-5-phenylprolinate in solution in 150 cm3 of anhydrous 1,2-dichloroethane and 3.9 g of ethyl (E)-3-aminocinnamate, 4.8 g of ethyl (E)-3-{3-[2-((2RS,5SR)-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}cinnamate are obtained [proton NMR (250 MHz, DMSO D6, δ in ppm, J in Hz), 2 rotamers at room temperature, peak coalescence at 120° C.: 1.3 (t, 3H, CH3); 1.5 (bs, 9H, (CH3)3); 4.25 (q, 2H, CH2O); 6.4 (d, 1H, J=15, CH= trans); 7.10 to 7.70 (m, 10H, aromatic and CH= trans). Infrared spectrum (KBr), characteristic bands in cm-1 : 3375, 3150, 3070, 3035, 2980, 2940, 2880, 1740, 1700, 1640, 1610, 1590, 1560, 1495, 1490, 1455, 1430, 1395, 1370, 1310, 1270, 1220, 1180, 1160, 1040, 990, 860, 840, 790, 760, 705, 685].
Sources & evidence
- ORD record
- ord-d93a4e4a52a34c00a45bae71fad82938
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610144
Reaction notes
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