Dimethyl Sulfoxide → HCID 87766776, compound

HRID 2225275Notes

Reaction equation

HRID 2225275 reaction equation
CS(C)=O.C(=O)=O.CC(C)=O.C(Cl)(=O)C(Cl)=O.[OH:18][CH2:19][C@H:20]1[C@@H:25]([NH:26][C:27](=[O:42])[CH2:28][NH:29][C:30](=[O:41])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[CH2:24][CH2:23][C@@H:22]([N:43]([CH:51]([CH3:53])[CH3:52])[C:44](=[O:50])[O:45][C:46]([CH3:49])([CH3:48])[CH3:47])[CH2:21]1.C(N(CC)CC)C>C(Cl)Cl>[CH:19]([C@H:20]1[C@@H:25]([NH:26][C:27](=[O:42])[CH2:28][NH:29][C:30](=[O:41])[C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=2)[CH2:24][CH2:23][C@@H:22]([N:43]([CH:51]([CH3:53])[CH3:52])[C:44](=[O:50])[O:45][C:46]([CH3:47])([CH3:48])[CH3:49])[CH2:21]1)=[O:18]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18522661Acetone cardiceHCID 69285460HCID 69285460, compound

Product 1

HCID 87766776HCID 87766776, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of DMSO (0.42 g, 5 mmol) in 30 ml of methylene chloride was cooled to −78° C. (dry ice-acetone bath) and treated drop-wise with oxalyl chloride (0.38 g, 3.0 mmol). After the addition was complete and solution was stirred for 30 minutes and then treated drop-wise with a solution of tert-butyl (1R,3R,4S)-3-(hydroxymethyl)-4-(2-(3-(trifluoromethyl)-benzamido)acetamido)cyclohexyl(isopropyl)carbamate (0.50 g, 0.97 mmol; see Example 8b, Step 6) in 20 ml of methylene chloride. After the addition was complete and solution was stirred for 40 minutes and then treated 1 ml of triethylamine (1 g, 10 mmol) and stirred for 30 minutes before removing the cooling bath and stirring at room temperature for 1 hour. The mixture was quench with 100 mL of saturated sodium bicarbonate and the organic layer was separated and washed successively with water and brine, and then dried over Na2SO4. The drying agent is filtered and the solvent removed on a rotary evaporator to give 0.45 mg of tert-butyl(1R,3R,4S)-3-formyl-4-(2-(3-(trifluoromethyl)benzamido)acetamido)-cyclohexyl(isopropyl)carbamate as a white solid which was used without further purification. MS found: (M+H)+=514.29.

Workup

  1. additionAfter the addition
  2. additionAfter the addition
  3. stirringsolution was stirred for 40 minutes
  4. stirringstirred for 30 minutes
  5. custombefore removing the cooling bath
  6. stirringstirring at room temperature for 1 hour
  7. customThe mixture was quench with 100 mL of saturated sodium bicarbonate
  8. customthe organic layer was separated
  9. washwashed successively with water and brine
  10. dry with materialdried over Na2SO4
  11. filtrationThe drying agent is filtered
  12. customthe solvent removed on a rotary evaporator

Sources & evidence

ORD record
ord-45a1b222285e48f48931a42b4035bc66
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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