2-Methylpyridine → (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonic acid

HRID 1006832Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006832
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][CH:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1C.Cl[S:43]([OH:46])(=[O:45])=[O:44]>ClCCl>[CH2:1]([O:8][CH2:9][C@@H:10]1[CH2:14][C@@H:13]([S:15][C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:12][N:11]1[S:43]([OH:46])(=[O:45])=[O:44])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 79752-MethylpyridineHCID 24638Chlorosulfonic acidHCID 226716602-Benzyloxymethyl-4-tritylsulfanyl-pyrrolidine

Produkt 1

HCID 69433587(2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine (0.435 g) in dichloromethane (30.0 ml) was treated with 2-picoline (2.11 ml) and chlorosulphonic acid (0.186 ml). The reaction mixture was stirred for 5 h at room temperature and evaporated to dryness. The residue was quenched with ice/water and extracted with EtOAc. The aqueous layer was saturated with sodium chloride and acidified with 1 molar HCl to pH 3.4 and extracted again with EtOAc. The organic phase was washed with brine, dried over magnesium sulphate and concentrated to obtain (2S,4R)-2-benzyloxymethyl-4-tritylsulfanyl-pyrrolidine-1-sulfonic acid (0.26 g) as an oil, MS: 544 (M−H)−.

Aufarbeitung

  1. customevaporated to dryness
  2. customThe residue was quenched with ice/water
  3. extractionextracted with EtOAc
  4. extractionextracted again with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3c9e2a98098e4908aa75f4551a30ec78
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790860B2

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