3-Aminobenzenesulfonic acid → 3-({[(2S)-2-amino-3-methoxy-3-oxopropoxy]carbonyl}amino)benzene-1-sulfonic acid

HRID 1468305Notes

Reaction equation

HRID 1468305 reaction equation
CC(OC([NH:8][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][OH:11])=O)(C)C.[NH2:16][C:17]1[CH:18]=[C:19]([S:23]([OH:26])(=[O:25])=[O:24])[CH:20]=[CH:21][CH:22]=1.Cl[C:28](Cl)([O:30]C(=O)OC(Cl)(Cl)Cl)Cl>N1C=CC=CC=1>[NH2:8][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:10][O:11][C:28]([NH:16][C:17]1[CH:18]=[C:19]([S:23]([OH:26])(=[O:24])=[O:25])[CH:20]=[CH:21][CH:22]=1)=[O:30]

Participants

5

Reactant 3

HCID 84743-Aminobenzenesulfonic acidHCID 94429TriphosgeneHCID 7019177N-Boc-L-serine methyl ester

Product 1

HCID 534690253-({[(2S)-2-amino-3-methoxy-3-oxopropoxy]carbonyl}amino)benzene-1-sulfonic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Boc-Ser-OMe, 110 mg (0.5 mmol), and 87 mg (0.5 mmol) of 3-aminobenzenesulfonic acid were dissolved in 1 ml of pyridine, and 50 mg of triphosgene was added to the solution. The mixture was stirred at room temperature for 2 hours and the solvent was then distilled off. The resulting residue was purified according to the purification step A to give the crude product of the protected title compound. The crude product obtained was dissolved in 1 ml of methylene chloride and 1 ml of trifluoroacetic acid. The solution was stirred for 30 minutes at room temperature. After the solvent was distilled off, the mixture was purified in accordance with the purification step A to give the title compound.

Workup

  1. distillationthe solvent was then distilled off
  2. customThe resulting residue was purified
  3. customaccording to the purification step A

Sources & evidence

ORD record
ord-9a504f2a86744fe9bcad050983ae129e
Source dataset
uspto-grants-2015_04
Patent number
US09000208B2

Reaction notes

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