Sodium Hydroxide → HCID 57650242, compound

HRID 2063469Notes

Reaction equation

HRID 2063469 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17](=O)[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1.[OH-].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][C:14](=[O:16])[CH3:15])[CH2:10][C@@H:9]1[C:17](=[S:37])[NH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 87949Lawesson's reagentHCID 57650275HCID 57650275, compound

Product 1

HCID 57650242HCID 57650242, compoundYield 84.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of purified (2R,4R)-tert-butyl-2-((4-chlorobenzyl)carbamoyl)-4-acetoxypyrrolidine-1-carboxylate from Step B (4.1 g, 10.3 mmol) and Lawesson's reagent (2.1 g, 5.15 mmol) in toluene (80 ml) was refluxed for 2 h under argon. The mixture was cooled to room temperature and then diluted with EtOAc (80 ml), treated with 1N NaOH (2×40 ml), dried over Na2SO4 and concentrated in vacuo. Flash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc) provided the desired product as a foamy white solid (1.8 g, 43%).

Workup

  1. temperaturewas refluxed for 2 h under argon
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customFlash chromatography purification (Hex/EtOAc gradient, 10-100% EtOAc)

Sources & evidence

ORD record
ord-daa4b6890a714d789f4668e6b9415df7
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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