2-{[(3-Methylphenyl)carbamoyl]amino}acetic acid → HCID 131719906, compound

HRID 975952Notes

Reaction equation

HRID 975952 reaction equation
[C:1]1([CH:7]2[NH:11][CH:10]([C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[NH:27][CH2:28][C:29](O)=[O:30])[CH:22]=[CH:23][CH:24]=1>ClCCCl.S(Cl)(Cl)=O>[CH3:18][C:19]1[CH:20]=[C:21]([NH:25][C:26](=[O:32])[NH:27][CH2:28][C:29]([N:11]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][CH:10]2[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[O:30])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 2

HCID 149969602-{[(3-Methylphenyl)carbamoyl]amino}acetic acidHCID 131719907HCID 131719907, compound

Product 1

HCID 131719906HCID 131719906, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 24386Thionyl ChlorideSolvent

Procedure

By proceeding in a fashion similar to that described in Example 1, but starting from 3 g of isopropyl (2RS,5SR)-5-phenylprolinate, 2.7 g of 2-[3-(3-methylphenyl)ureido]acetic acid in a suspension in 75 cm3 of anhydrous 1,2-dichloroethane and 1 cm3 of sulphinyl chloride, 1.2 g of isopropyl (2RS,5SR)-1-{2-[3-(3-methylphenyl)ureido]acetyl}-5-phenylprolinate are obtained after purification [proton NMR (200 MHz, CDCl3, δ in ppm), 2 rotamers at room temperature, preponderant rotamer description: 1.1 (d, 6H, (CH3)2); 1.7 to 2.5 (m, 4H, H in position 3 and 4 on pyrrolidine); 2.15 (s, 3H, CH3); 3 and 4.1 (2bd, 2H, CH2N); 4.4 (bt, 1H, H in position 2 on pyrrolidine); 4.9 (m, 2H, isopropyl CH and H in position 5 on pyrrolidine); 6.6 to 7.5 (m, 9H, aromatic). Infrared spectrum (KBr), characteristic bands in cm-1 : 3365, 3150, 3060, 3030, 2980, 2935, 2875, 1738, 1700, 1645, 1615, 1595, 1560, 1495, 1450, 1430, 1375, 1305, 1295, 1280, 1210, 1190, 1145, 1120, 915, 890, 860, 780, 755 705].

Sources & evidence

ORD record
ord-0e731b6836994ba7850dd65973c3d522
Source dataset
uspto-grants-1997_03
Patent number
US05610144

Reaction notes

Loading…