Pyridine → (2S)-2-amino-3-{[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]amino}propanoic acid

HRID 1773088Notes

Reaction equation

HRID 1773088 reaction equation
Cl.C([O:6][C:7](=[O:19])[C@H:8]([CH2:17][NH2:18])[NH:9]C(OC(C)(C)C)=O)(C)(C)C.[NH2:20][C:21]1[C:22]([OH:32])=[C:23]([S:28]([OH:31])(=[O:30])=[O:29])[CH:24]=[C:25]([Cl:27])[CH:26]=1.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl.N1C=CC=CC=1>C(Cl)Cl>[NH2:9][C@@H:8]([CH2:17][NH:18][C:34](=[O:36])[NH:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([S:28]([OH:31])(=[O:30])=[O:29])[C:22]=1[OH:32])[C:7]([OH:6])=[O:19]

Participants

6

Reactant 4

HCID 1049PyridineHCID 69273-Amino-5-chloro-2-hydroxybenzenesulfonic acidHCID 94429TriphosgeneHCID 86679032(S)-tert-Butyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate hydrochloride

Product 1

HCID 53377991(2S)-2-amino-3-{[(5-chloro-2-hydroxy-3-sulfophenyl)carbamoyl]amino}propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

297 mg (1 mmol) of 3-amino-N-(tert-butoxycarbonyl)-L-alanine tert-butylester hydrochloride, 223 mg (1 mmol) of 3-amino-5-chloro-2-hydroxybenzenesulfonic acid and 100 mg (0.33 mmol) of triphosgene were suspended in methylene chloride (3 ml), added with 0.8 ml of pyridine, and stirred at room temperature overnight. The solvent was distilled away, and the resultant residue was purified by employing purification step A to obtain the title compound in protected form. To the resulting protected form, 3 ml of trifluoroacetic acid was added, and the resultant was stirred for 5 hours. Subsequently, the solvent was distilled away and the obtained residue was purified using purification step A to obtain the title compound.

Workup

  1. distillationThe solvent was distilled away
  2. customthe resultant residue was purified
  3. custompurification step A

Sources & evidence

ORD record
ord-6da356e5e2dd435193d4a9503209f595
Source dataset
uspto-grants-2016_02
Patent number
US09253997B2

Reaction notes

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