Dichloromethane → HCID 60094104, compound

HRID 2307287Notes

Reaction equation

HRID 2307287 reaction equation
[N+](C1C=CC(C([O:10][C@H:11]([C@H:18]2[CH2:23][O:22][CH2:21][C:20](=[O:24])[NH:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=O)=CC=1)([O-])=O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:10][C@@H:11]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C@@H:18]1[NH:19][C:20](=[O:24])[CH2:21][O:22][CH2:23]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 60094108HCID 60094108, compound

Product 1

HCID 60094104HCID 60094104, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-((3R)-5-Oxomorpholin-3-yl)(phenyl)methyl 4-nitrobenzoate (Preparation 7, 1.2 g) is treated with dichloromethane (10 mL), ethanol (30 mL) and potassium carbonate (1.0 g). After 2 h, the reaction mixture is filtered and the filtered solid is triturated with ethanol-dichloromethane (3:1 v:v, 3×30 mL). The filtrates are combined and concentrated under reduced pressure. The resulting residue is adsorbed onto silica gel and purified by flash column chromatography (methanol/CH2Cl2, 1-6%) to afford 0.61 g of the title compound. Physical characteristics. 1H NMR (400 MHz, DMSO-d6) δ 7.55, 7.4-7.2, 5.65, 4.61, 3.92, 3.9-3.8, 3.65-3.55, 3.44.

Workup

  1. filtrationthe reaction mixture is filtered
  2. customthe filtered solid is triturated with ethanol-dichloromethane (3:1 v:v, 3×30 mL)
  3. concentrationconcentrated under reduced pressure
  4. custompurified by flash column chromatography (methanol/CH2Cl2, 1-6%)

Sources & evidence

ORD record
ord-0244d7db77cf4345b2164cfe4a1fcc3b
Source dataset
uspto-grants-2004_12
Patent number
US06831081B2

Reaction notes

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