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

HRID 2402936Notes

Reaction equation

HRID 2402936 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

100 mg (0.38 mmol) of Boc-Ser-OtBu, 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 thereto. After stirring the mixture at room temperature overnight, a solvent was removed. Purification was conducted in accordance with the purification process A to obtain a protected form of a title compound. The obtained protected form was dissolved in 2 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. customa solvent was removed
  2. customPurification

Sources & evidence

ORD record
ord-329799f45e4b49e38ecb8a55bcc8ba28
Source dataset
uspto-grants-2014_08
Patent number
US08796485B2

Reaction notes

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