Dichloromethane → N5-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine
Reaction equation
C(Cl)Cl.[NH:4](C(OC(C)(C)C)=O)[C@H:5]([C:11]([O:13]C(C)(C)C)=[O:12])[CH2:6][CH2:7][C:8](=[O:10])O.Cl.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:38][C:39]1[CH:40]=[C:41]([Cl:50])[C:42]([CH3:49])=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=1>FC(F)(F)C(O)=O.C1COCC1>[Cl:50][C:41]1[CH:40]=[C:39]([NH:38][C:8](=[O:10])[CH2:7][CH2:6][C@@H:5]([C:11]([OH:13])=[O:12])[NH2:4])[CH:44]=[C:43]([S:45]([OH:48])(=[O:47])=[O:46])[C:42]=1[CH3:49]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
After 1 ml of methylene chloride and 1 ml of THF were added to 303 mg (1 mmol) of Boc-Glu-OtBu hydrochloride and 180 mg (1.1 mmol) of CDI, 221 mg of 5-amino-3-chloro-2-methylbenzenesulfonic acid was further added to mixture. The mixture was stirred at room temperature overnight and then purified in accordance with the purification step A to give the protected form of the intended product. The obtained protected product was dissolved in 5 ml of trifluoroacetic acid. The solution was stirred for 2 hours. The solvent was distilled off and the mixture was purified in accordance with the purification step A to give the title compound.
Workup
- additionwas further added to mixture
- custompurified in accordance with the purification step A
- customto give the protected form of the intended product
- stirringThe solution was stirred for 2 hours
- distillationThe solvent was distilled off
- customthe mixture was purified in accordance with the purification step A
Sources & evidence
- ORD record
- ord-ae33a03fa29a405c9b2430df8fc014b1
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08877739B2
Reaction notes
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