Chloroform → Methyl N1-[2-[(4-chlorophenyl)carbonyl]-4-(methyloxy)phenyl]-N2-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-alpha-asparaginate
Reaction equation
C[N:2]([C:11]([O:13][CH2:14][CH:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:12])[C@H:3]([C:8](Cl)=[O:9])[CH2:4][C:5](=[O:7])[OH:6].[NH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][C:30]=1[C:37]([C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)=[O:38].[CH:46](Cl)(Cl)Cl>>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([C:37]([C:30]2[CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[CH:34][C:29]=2[NH:28][C:8](=[O:9])[C@H:3]([CH2:4][C:5]([O:6][CH3:46])=[O:7])[NH:2][C:11]([O:13][CH2:14][CH:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[C:22]3[C:27]2=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:12])=[O:38])=[CH:40][CH:41]=1Participants
4
Reactant 3
Product 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of Methyl N-{[(9H-fluoren-9-ylmethyl)oxy]carbonyl}-L-α-aspartyl chloride (prepared from J. Org. Chem. 1990, 55, 3068-3074 and J. Chem. Soc. Perkin Trans. 1 2001, 1673-1695) (221 g, 0.57 mol) and [2-amino-5-(methyloxy)phenyl](4-chlorophenyl)methanone (for a preparation see Intermediate 7) (133 g, 0.5 mol) in CHCl3 (410 mL) was stirred at 60° C. for 1.5 h before being cooled and concentrated under reduced pressure and used without further purification. LC/MS: m/z 613 [M(35Cl)+H]+, Rt=3.89 min.
Workup
- temperaturebefore being cooled
- concentrationconcentrated under reduced pressure
- customused without further purification
Sources & evidence
- ORD record
- ord-130b3c9341e44780a9503cc14b7efe92
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09023842B2
Reaction notes
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