Dimethyl Sulfoxide → HCID 59857999, compound

HRID 2378342Notes

Reaction equation

HRID 2378342 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16](=[O:38])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH:25]2[CH:29]([OH:30])[CH2:28][N:27]([CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH2:26]2)[N:19]=1)([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[C:11]([O:15][C:16](=[O:38])[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH:25]2[C:29](=[O:30])[CH2:28][N:27]([CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[CH2:26]2)[N:19]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59858004HCID 59858004, compound

Product 1

HCID 59857999HCID 59857999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of DMSO (0.02 mol) in 30 mL of anhydrous CH2Cl2 was added dropwise oxalyl chloride (0.015 mol). The mixture was stirred at −78° C. for 10 min. After this time a solution of [6-(1-benzyl-4-hydroxy-pyrrolidin-3-ylmethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester I-3 (0.01 mol) in 10 mL of anhydrous CH2Cl2 was added dropwise at a rate to keep the reaction temperature below −60° C. Upon complete addition, the mixture was allowed to stir at −78° C. for 2 h. Then anhydrous triethylamine (0.03 mol) was added dropwise to the mixture. After complete addition, the reaction mixture was allowed to warm to room temperature. The resulting solution was partitioned between 1 M NaOH (40 ml) and the product was extracted with CH2Cl2 (30 ml×2). All organic layers were combined, washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to yield crude product, which was purified using column chromatography (silica gel, CH2Cl2:EtOAc, 4:1) (87%).

Workup

  1. customthe reaction temperature below −60° C
  2. additionUpon complete addition
  3. stirringto stir at −78° C. for 2 h
  4. additionAfter complete addition
  5. temperatureto warm to room temperature
  6. customThe resulting solution was partitioned between 1 M NaOH (40 ml)
  7. extractionthe product was extracted with CH2Cl2 (30 ml×2)
  8. washwashed with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. customto yield crude product, which
  12. customwas purified

Sources & evidence

ORD record
ord-ea898a5603d3425bb2c2db0067327b8c
Source dataset
uspto-grants-2008_12
Patent number
US07470790B2

Reaction notes

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