Dichloromethane → N5-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine

HRID 705454Notes

Reaction equation

HRID 705454 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

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 808054-Amino-6-chlorotoluene-2-sulphonic acidHCID 131731743Boc-Glu-OtBu hydrochloride

Product 1

HCID 45275785N5-(3-chloro-4-methyl-5-sulfophenyl)-L-glutamine

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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 added thereof and stirred at room temperature overnight. Purification was conducted in accordance with the purification process A to obtain a protected form of the intended compound. The obtained protected form was dissolved in 5 mL of a trifluoroacetic acid and stirred for 2 hours. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a title compound.

Workup

  1. customPurification
  2. customA to obtain a protected form of the intended compound
  3. stirringstirred for 2 hours
  4. customAfter removing
  5. customa solvent, purification

Sources & evidence

ORD record
ord-eb523be1bd4c413b89206d19fc64b93d
Source dataset
uspto-grants-2015_11
Patent number
US09174932B2

Reaction notes

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