Dimethyl Sulfoxide → HCID 86600472, compound

HRID 1454246Notes

Reaction equation

HRID 1454246 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[C:11]([O:15][C:16](=[O:30])[NH:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@:19]1([CH2:28][OH:29])[CH2:24][CH2:25][CH2:26][OH:27])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:30])[NH:17][C@@H:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@:19]1([CH:28]=[O:29])[CH2:24][CH2:25][CH:26]=[O:27])([CH3:14])([CH3:12])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69044834HCID 69044834, compound

Product 1

HCID 86600472HCID 86600472, compoundYield 0.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of dimethyl sulfoxide (16 g, 180 mmol) in dichloromethane (60 mL) was cooled to −78° C. in a cooling bath and treated dropwise with oxalyl chloride (14.2 g, 112 mmol). After the addition was complete, the solution was stirred for 30 minutes and then treated dropwise with a solution of [(1R,2S)-2-hydroxymethyl-2-(3-hydroxypropyl)-cyclohexyl]-carbamic acid tert-butyl ester (4.8 g, 16.7 mol) in dichloromethane (100 mL). After the addition was complete, the solution was stirred for 40 minutes and then treated with triethylamine (19 g, 190 mmol). The mixture was stirred for 30 minutes. The cooling bath was removed and the mixture was allowed to warm to room temperature where it stirred for 1 hour. The mixture was quenched with saturated aqueous sodium bicarbonate (100 mL). The organic phase was removed, 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 (4.75 g). 1H NMR (300 MHz, CDCl3) δ9.78 (s, 1H), 9.41 (s, 1H), 4.56 (bd, J=9 Hz, 1H), 4.05 (m, 1H), 2.60-1.30 (m, 21H).

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. customThe cooling bath was removed
  6. stirringstirred for 1 hour
  7. customThe mixture was quenched with saturated aqueous sodium bicarbonate (100 mL)
  8. customThe organic phase was removed
  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-e70929eafb734f27bae5325eba9af227
Source dataset
uspto-grants-2009_01
Patent number
US07479496B2

Reaction notes

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