Triethylamine → HCID 57526983, compound

HRID 1452565Notes

Reaction equation

HRID 1452565 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20]O)[O:17][C:16]2=[O:22])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:35]=[N+:36]=[N-:37].[Na+]>ClCCl.O>[F:1][C:2]1[CH:3]=[C:4]([N:15]2[CH2:19][C@H:18]([CH2:20][N:35]=[N+:36]=[N-:37])[O:17][C:16]2=[O:22])[CH:5]=[C:6]([F:14])[C:7]=1[N:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 57526976HCID 57526976, compound2×

Product 1

HCID 57526983HCID 57526983, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(5R)-3-[3,5-difluoro-4-(4-thiomorpholinyl)phenyl]-5-(hydroxymethyl)-oxazolidin-2-one (Intermediate 12) (15 g, 45.5 mmol) was dissolved in a mixture of triethylamine (9.6 ml, 68 mmol) and dichloromethane (200 ml). The resulting solution was cooled to 0° C. and methane sulfonyl chloride (4.6 ml, 59 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours then allowed to warm to room temperature. Water (200 ml) was added and then the organic layer separated, dried over magnesium sulfate, filtered and concentrated in vacuo. This intermediate was dissolved in dry DMF (120 ml). Sodium azide (11.8 g, 181 mmol) was added and the reaction mixture stirred at 70° C. overnight. It was diluted with dichloromethane (700 ml), washed with water (200 ml) and brine (200 ml) and dried over magnesium sulfate. Concentration in vacuo gave 16 g of the title compound.

Workup

  1. temperatureto warm to room temperature
  2. customthe organic layer separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThis intermediate was dissolved in dry DMF (120 ml)
  7. stirringthe reaction mixture stirred at 70° C. overnight
  8. washwashed with water (200 ml) and brine (200 ml)
  9. dry with materialdried over magnesium sulfate
  10. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3ab2f15d97fb4d279134c09cb15b4ea0
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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