Triethylamine → HCID 89894133, compound

HRID 925428Notes

Reaction equation

HRID 925428 reaction equation
O[CH2:2][C@H:3]1[O:7][C:6](=[O:8])[N:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.C(N(CC)CC)C.[CH3:24][S:25](Cl)(=O)=O.C[S-].[Na+]>C(Cl)Cl.CN(C=O)C>[CH3:24][S:25][CH2:2][C@H:3]1[O:7][C:6](=[O:8])[N:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 4378561Sodium methanethiolateHCID 89894011HCID 89894011, compound

Product 1

HCID 89894133HCID 89894133, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a turbid solution of (S)-tert-butyl 5-(hydroxymethyl)-2-oxooxazolidin-3-ylcarbamate (800 mg, 3.44 mmol) in DCM (5 mL), triethylamine (436 mg, 4.31 mmol) and methanesulfonyl chloride (493 mg, 4.31 mmol) were added and the reaction was stirred, at r.t., under nitrogen for 1 h 30 min. Conversion into the corresponding methanesulfonyl intermediate was complete. The solution was washed with cold citric acid (pH=4-5) and cold brine and the organic layer was separated and dried over Na2SO4. Evaporation of the solvent at 32° C. yielded a colourless foam (980 mg; yield=92%) that was dissolved in DMF (5 mL). Sodium methanethiolate (302 mg, 4.31 mmol) was added and the mixture stirred at 60° C. for 1 h. Conversion into the title product was complete. AcOEt was added and the solution was washed with cold citric acid (pH=3-4), then cold water and cold brine.

Workup

  1. washThe solution was washed with cold citric acid (pH=4-5) and cold brine
  2. customthe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent at 32° C.
  5. customyielded a colourless foam (980 mg; yield=92%) that
  6. stirringthe mixture stirred at 60° C. for 1 h

Sources & evidence

ORD record
ord-06ce2b53b9f84d64a77af18f76afb419
Source dataset
uspto-grants-2016_03
Patent number
US09284306B2

Reaction notes

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