Dichloromethane → HCID 72208118, compound

HRID 1697696Notes

Reaction equation

HRID 1697696 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([S:10]C(=O)C)[CH2:7][N:6]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:4].ClCCl.C(=O)([O-])[O-].[K+].[K+]>CO>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([SH:10])[CH2:7][N:6]1[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86646860HCID 86646860, compound

Product 1

HCID 72208118HCID 72208118, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S,4R)-4-acetylsulfanyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (12.5 g, 41 mmol; CAS Reg. No. 188111-18-4) in MeOH (200 ml) and dichloromethane (20 ml) was added potassium carbonate (5.7 g, 41.2 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 1 h. After the starting material was consumed the solvent was evaporated. The residue was dissolved in water and extracted with EtOAc (2×200 ml). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and evaporated to get the crude title compound (9.5 g, 36.1 mmol; 88%) which was used in next step without further purification. MS (ESI): m/z=262.0 [M+H]+.

Workup

  1. customAfter the starting material was consumed the solvent
  2. customwas evaporated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted with EtOAc (2×200 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-062e09fd19224ce8b62eadebe7244bfa
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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