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

HRID 1773088
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HRID 1773088 반응식
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]
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-6da356e5e2dd435193d4a9503209f595
출처 데이터셋
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09253997B2

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