Triethylamine → HCID 86675642, compound

HRID 1891401Notes

Reaction equation

HRID 1891401 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:4][C:3]=1[N:16]1[CH2:20][CH:19]2[CH2:21][C:22]3([CH2:27][CH:18]2[CH2:17]1)[O:26][CH2:25][CH2:24][O:23]3.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][O:14][S:36]([CH3:35])(=[O:38])=[O:37])[O:10][C:9]2=[O:15])[CH:5]=[CH:4][C:3]=1[N:16]1[CH2:20][CH:19]2[CH2:21][C:22]3([CH2:27][CH:18]2[CH2:17]1)[O:26][CH2:25][CH2:24][O:23]3

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 71182943HCID 71182943, compound

Product 1

HCID 86675642HCID 86675642, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

21.4 g (56.6 mmol) of 2-[2-fluoro-4-[(5R)-5-(hydroxymethyl)-2-oxo-3-oxazolidinyl]phenyl]-hexahydro-1H-spiro[cyclopenta[c]pyrrol-5,2′-[1,3]dioxolane] prepared in the step 7 was dissolved in 200 ml of methylene chloride, 19.7 ml (141.5 mmol) of triethylamine was added, the temperature was lowered to 0° C., and then, 8.76 ml (113.2 mmol) of methansulfonyl chloride was added dropwise over 15 minutes, and the mixture was stirred for 1 hour. After the reaction was completed, the reaction mixture was diluted with 200 mL of methylene chloride, washed with water and a saturated aqueous solution of sodium chloride, and then, dried over magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound.

Workup

  1. customwas lowered to 0° C.
  2. washwashed with water
  3. dry with materiala saturated aqueous solution of sodium chloride, and then, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0cd81237d9b74d3fa6520ab866114c0e
Source dataset
uspto-grants-2013_08
Patent number
US08507540B2

Reaction notes

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