Triethylamine → HCID 86635670, compound

HRID 2388709Notes

Reaction equation

HRID 2388709 reaction equation
[OH:1][CH2:2][C:3]1[S:4][C:5]2[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:9][C:10]=2[N:11]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[CH3:26][S:27]([O:1][CH2:2][C:3]1[S:4][C:5]2[CH2:6][N:7]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:9][C:10]=2[N:11]=1)(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68643978HCID 68643978, compound

Product 1

HCID 86635670HCID 86635670, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane solution (15 ml) of tert-butyl 2-(hydroxymethyl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (1 eq.) was added triethylamine (2.5 eq.) and methane sulfonylchloride (1.2 eq.) at 0° C. and the resulting reaction mixture was stirred at ambient temperature for 2 h. The reaction was quenched with ice and diluted with dichloromethane. The organic layer was successively washed with water and brine and finally dried over sodium sulfate. Evaporation of the organic layer under reduced pressure gave the crude product which was used directly in the next step without further purification. Yield: 80%.

Workup

  1. customthe resulting reaction mixture
  2. customThe reaction was quenched with ice
  3. additiondiluted with dichloromethane
  4. washThe organic layer was successively washed with water and brine
  5. dry with materialfinally dried over sodium sulfate
  6. customEvaporation of the organic layer under reduced pressure

Sources & evidence

ORD record
ord-21b3ec9a1c894fe6b4a473f6a62f7456
Source dataset
uspto-grants-2012_09
Patent number
US08268814B2

Reaction notes

Loading…