Acetyl chloride → HCID 57550254, compound

HRID 548644Notes

Reaction equation

HRID 548644 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][C@H:7]1[N:11]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][CH:23]3[CH3:27])=[CH:14][CH:13]=2)[C:10](=[O:28])[CH2:9][CH2:8]1>ClCCl>[CH3:27][CH:23]1[CH2:24][CH2:25][CH2:26][N:22]1[CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:11]2[C:10](=[O:28])[CH2:9][CH2:8][C@H:7]2[CH2:6][NH:5][C:1](=[O:3])[CH3:2])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 57550255HCID 57550255, compound

Product 1

HCID 57550254HCID 57550254, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.51 ml, 0.72 mmol, 1.2 eq) is added to a cooled (ice bath) solution of (5S)-5-(aminomethyl)-1-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}pyrrolidin-2-one 113 (0.2 g, 0.6 mmol, 1 eq) in dichloromethane (12 ml). The mixture is stirred 2 hours at room temperature, washed with a saturated solution of sodium bicarbonate and with brine, dried over magnesium sulfate and concentrated under vacuum to give 0.158 g of yellow oil. The crude material is purified by two chromatographies over silicagel (first one: gradient dichloromethane/methanol/ammonia 100:0:0 to 88:12:1.2; second one: dichloromethane/methanol/ammonia 80:20:2).

Workup

  1. washwashed with a saturated solution of sodium bicarbonate and with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08130acae2924b3da167fcf645cb7b8b
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

Loading…