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

HRID 890577

反応式

HRID 890577 の反応式
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]

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9f53c9452f294edf8695ae1906d4800c
出典データセット
uspto-grants-2006_02
特許番号
US06998233B2

関連ノート

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