Sodium Carbonate → (2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

HRID 890577노트

반응식

HRID 890577 반응식
Cl.C[O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.Cl[S:12]([C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O>O.CN(C)C=O.ClCCl.C(N(CC)CC)C.N1C=CC=CC=1>[S:12]([N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:4]([OH:3])=[O:10])([C:15]1[CH:23]=[CH:22][C:18]([CH3:19])=[CH:17][CH:16]=1)(=[O:14])=[O:13]

참가 물질

10

반응물 4

HCID 10340Sodium CarbonateHCID 823854-(Chlorosulfonyl)benzoic acidHCID 2733200methyl L-prolinate hydrochlorideHCID 4327891Pentafluorophenyl Trifluoroacetate

생성물 1

HCID 691957(2S)-1-(4-methylbenzenesulfonyl)pyrrolidine-2-carboxylic acid

시약·촉매·용매 5

HCID 962Water용매HCID 1049Pyridine용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

N-tosyl-proline derivatives were synthesized as follows. Proline methyl ester hydrochloride was reacted with 4-(chlorosulfonyl)benzoic acid and sodium carbonate in water. The product was converted to the pentafluorophenyl ester by reacting it with pentafluorophenyl trifluoroacetate and pyridine in N,N-dimethylformamide, and purified via flash chromatography. This activated ester was then reacted with the methyl-ester of glutamate (or any of the other amino acids tested) in the presence of triethylamine and dichloromethane, the product purified by flash chromatography, and the methyl esters hydrolyzed with lithium hydroxide in water. The final products were purified via reverse-phase HPLC and lyophilized.

후처리

  1. custompurified via flash chromatography
  2. customThis activated ester was then reacted with the methyl-ester of glutamate (or any of the other amino acids
  3. customthe product purified by flash chromatography
  4. customThe final products were purified via reverse-phase HPLC

출처 및 근거

ORD 기록
ord-9f53c9452f294edf8695ae1906d4800c
출처 데이터셋
uspto-grants-2006_02
특허 번호
US06998233B2

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