Methanesulfonyl chloride → (2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1527337Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1527337
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[F:24])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26][S:27](Cl)(=[O:29])=[O:28]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([O:13][S:27]([CH3:26])(=[O:29])=[O:28])[C@H:9]1[C:14](=[O:25])[NH:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:18]=1[F:24])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 68283845(2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 86673824(2S,3S)-2-(3-Chloro-2-fluoro-benzylcarbamoyl)-3-methanesulfonyloxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To an ice-cooled solution of (2S,3S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.98 g, 2.64 mmol) in dry pyridine (13 mL) was added methanesulfonyl chloride (0.31 mL, 3.96 mmol). The reaction was stirred at 0° C. for 2 h and then at RT for 72 h. The volatiles were evaporated in vacuo and the residue was partitioned between water and EtOAc. The aqueous layer was repeatedly extracted with EtOAc, the combined organics were washed with 0.1N HCl and brine, dried (phase separator) and concentrated in vacuo to afford the title compound. Brown oil. MS (LC-MS): 451 [M+H]+, 395 [MH−tBu]+, 351 [MH−Boc]+; tR (HPLC conditions c): 5.08 min. The material thus obtained was used without any purification.

Aufarbeitung

  1. waitat RT for 72 h
  2. customThe volatiles were evaporated in vacuo
  3. customthe residue was partitioned between water and EtOAc
  4. extractionThe aqueous layer was repeatedly extracted with EtOAc
  5. washthe combined organics were washed with 0.1N HCl and brine
  6. customdried (phase separator)
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9c359254899f4e55969c25d87e6739c4
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085555B2

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