Dimethyl Sulfoxide → HCID 86600471, compound

HRID 1454240Notes

Reaction equation

HRID 1454240 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19](=[O:33])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@:22]1([CH2:31][OH:32])[CH2:27][CH2:28][CH2:29][OH:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH2:11]([O:18][C:19](=[O:33])[NH:20][C@@H:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@:22]1([CH:31]=[O:32])[CH2:27][CH2:28][CH:29]=[O:30])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69038963HCID 69038963, compound

Product 1

HCID 86600471HCID 86600471, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethyl sulfoxide (1.6 g, 19 mmol) in dichloromethane (50 mL) was cooled to −78° C. and treated dropwise with oxalyl chloride (1.42 g, 11.2 mmol). After the addition was complete, the solution was stirred for 30 minutes and was then treated dropwise with a solution of [(1R,2S)-2-hydroxymethyl-2-(3-hydroxypropyl)-cyclohexyl]-carbamic acid benzyl ester (0.65 g, 1.9 mmol) in dichloromethane (10 mL). After the addition was complete, the solution was stirred for 40 minutes and then treated with triethylamine (1.8 g, 18 mmol). The mixture was stirred for 30 minutes before removing the cooling bath and stirring at room temperature for 1 hour. The mixture was quenched with saturated aqueous sodium bicarbonate (100 mL) and the organic phase was separated and washed successively with water and saturated aqueous sodium chloride, and then dried over sodium sulfate. The solvent was removed under vacuum to give an oil (0.6 g). 1H NMR (300 MHz, CDCl3) δ9.74 (bs, 1H), 9.43 (bs, 1H), 7.39-7.27 (m, 5H), 5.06 (m, 2H), 4.91 (bd, J=9 Hz, 1H), 4.14 (bm, 1H), 2.60-1.30 (m, 12H). Mass spec (ES+) m/z 318.2 (M+H+, 100%).

Workup

  1. additionAfter the addition
  2. additionAfter the addition
  3. stirringthe solution was stirred for 40 minutes
  4. stirringThe mixture was stirred for 30 minutes
  5. custombefore removing the cooling bath
  6. stirringstirring at room temperature for 1 hour
  7. customThe mixture was quenched with saturated aqueous sodium bicarbonate (100 mL)
  8. customthe organic phase was separated
  9. washwashed successively with water and saturated aqueous sodium chloride
  10. dry with materialdried over sodium sulfate
  11. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-6f02f92ac394453c9283f06b8d0c880f
Source dataset
uspto-grants-2009_01
Patent number
US07479496B2

Reaction notes

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