Pyridine → (S)-2-[3-(6-Hydroxy-naphthalen-1-yl)-ureido]-pentanedioic acid 5-tert-butyl ester 1-methyl ester

HRID 581690Notes

Reaction equation

[NH2:1][C@H:2]([C:12]([O:14][CH3:15])=[O:13])[CH2:3][CH2:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].N1C=CC=CC=1.[C:22](Cl)(Cl)=[O:23].C1(C)C=CC=CC=1.[NH2:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([OH:44])=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1>ClCCl>[CH3:15][O:14][C:12](=[O:13])[C@@H:2]([NH:1][C:22]([NH:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([OH:44])=[CH:41][CH:42]=2)[CH:37]=[CH:36][CH:35]=1)=[O:23])[CH2:3][CH2:4][C:5]([O:6][C:7]([CH3:9])([CH3:10])[CH3:8])=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

To H-Glu(OtBu)-OCH3 (2.0 mmol, 0.50 g) in dichloromethane (25 mL) at 0° C. was added pyridine (8 mmol, 0.66 mL) then followed by dropwise addition of phosgene in toluene (3.0 mmol, 1.60 mL, 1.92 M). After stirring at 0° C. for 2 hours, 1-amino-6-naphthol (2.0 mmol, 0.32 g) was added in dichloromethane. After stirring at room temperature for 12 hours, the reaction mixture was evaporated to dryness and purified on silica gel (1:19, methanol/dichloromethane) to provide product as a light brown solid (0.71 g, 88%).

Workup

stirringAfter stirring at room temperature for 12 hours
customthe reaction mixture was evaporated to dryness
custompurified on silica gel (1:19, methanol/dichloromethane)

Sources & evidence

ORD record: ord-dddc69305f2d4491bdbba943e152c5e4
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05922697

Reaction notes

Loading…