Methanesulfonyl chloride → HCID 59764752、化合物

HRID 406472ノート

反応式

HRID 406472 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[C:5]([NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([OH:16])[CH2:12]1)=[O:10])=[O:6].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[C:5]([NH:7][CH2:8][C:9]([N:11]1[CH2:15][CH2:14][CH:13]([O:16][S:22]([CH3:21])(=[O:24])=[O:23])[CH2:12]1)=[O:10])=[O:6]

参加物

4

反応物 2

HCID 31297Methanesulfonyl chlorideHCID 59764665HCID 59764665、化合物

生成物 1

HCID 59764752HCID 59764752、化合物収率 98%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

A suspension of 3,4-dichloro-N-[2-(3-hydroxy-pyrrolidin-1-yl)-2-oxo-ethyl]-benzamide (2.00 g, 6.30 mol) in pyridine (40 mL) was heated at about 50° C. until the solution became homogenous and then cooled to about 0° C. Methanesulfonyl chloride (1.46 mL, 18.9 mol) was added to the reaction mixture dropwise. The reaction mixture was allowed to warm to room temperature and then concentrated in vacuo. The residue was dissolved in DCM (50 mL), washed with brine (2×50 mL), and the organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to give methanesulfonic acid 1-[2-(3,4-dichloro-benzoylamino)-acetyl]-pyrrolidin-3-yl ester (2.46 g, 98%) as a brown oil which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method n) Rt 1.76 min; m/z: (M+H)+ 395.

後処理

  1. temperaturecooled to about 0° C
  2. temperatureto warm to room temperature
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM (50 mL)
  5. washwashed with brine (2×50 mL)
  6. customthe organic portion was separated
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-c37aad7876aa4f34b90640f46fe7feb3
出典データセット
uspto-grants-2014_06
特許番号
US08754107B2

反応ノート

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