Methanesulfonyl chloride → HCID 59764752, compound
Reaction equation
[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]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
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.
Workup
- temperaturecooled to about 0° C
- temperatureto warm to room temperature
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in DCM (50 mL)
- washwashed with brine (2×50 mL)
- customthe organic portion was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-c37aad7876aa4f34b90640f46fe7feb3
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754107B2
Reaction notes
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