4-Amino-6-chlorotoluene-2-sulphonic acid → O-{[(3-chloro-4-methyl-5-sulfophenyl)amino]carbonyl}-L-serine

HRID 330867Notes

Reaction equation

HRID 330867 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:5]([O:7]C(C)(C)C)=[O:6])CO.[NH2:19][C:20]1[CH:21]=[C:22]([Cl:31])[C:23]([CH3:30])=[C:24]([S:26]([OH:29])(=[O:28])=[O:27])[CH:25]=1.ClC(Cl)(O[C:36](=[O:42])[O:37][C:38](Cl)(Cl)Cl)Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:31][C:22]1[CH:21]=[C:20]([NH:19][C:36]([O:37][CH2:38][C@@H:2]([C:5]([OH:7])=[O:6])[NH2:1])=[O:42])[CH:25]=[C:24]([S:26]([OH:29])(=[O:27])=[O:28])[C:23]=1[CH3:30]

Participants

6

Reactant 4

HCID 808054-Amino-6-chlorotoluene-2-sulphonic acidHCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 7019054Boc-Ser-Otbu

Product 1

HCID 45275789O-{[(3-chloro-4-methyl-5-sulfophenyl)amino]carbonyl}-L-serine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-Ser-OtBu, 100 mg (0.38 mmol), 86 mg (0.38 mmol) of 5-amino-3-chloro-2-methylbenzenesulfonic acid and 37 mg (0.0127 mmol) of triphosgene were suspended in 1 ml of methylene chloride, and 66 μl (0.76 mmol) of DIEA was added to the suspension. After stirring at room temperature overnight, the solvent was removed by distillation. The mixture was purified according to the purification step A to give the protected title compound. The protected product obtained was dissolved in 2 ml of trifluoroacetic acid and stirred for 2 hours. The solvent was then removed by distillation and the mixture was purified according to the purification step A to give the title compound.

Workup

  1. customthe solvent was removed by distillation
  2. customThe mixture was purified
  3. customaccording to the purification step A

Sources & evidence

ORD record
ord-715ab3645524440fab104abf76bc6b00
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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