Triethylamine → HCID 60133546, compound

HRID 723750Notes

Reaction equation

HRID 723750 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][OH:23])[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH3:33][S:34](Cl)(=[O:36])=[O:35]>ClCCl>[O:1]1[C:5]2([CH2:6][CH2:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[CH2:21][C@H:20]([CH2:22][O:23][S:34]([CH3:33])(=[O:36])=[O:35])[O:19][C:18]4=[O:24])=[CH:13][C:12]=3[F:25])[CH2:9][CH2:10]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21356569HCID 21356569, compound

Product 1

HCID 60133546HCID 60133546, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-(4-(1,4-Dioxa-8-azaspiro[4,5]dec-8-yl)-3-fluorophenyl)-5-hydroxymethyloxazolidin-2-one (4.024 g, 11.43 mM) was dissolved in dichloromethane (200 ml), and treated with triethylamine (1.45 g, 14.4 mM), then cooled under nitrogen to 0°. Methanesulfonyl chloride (1.32 g, 11.5 mM) was added dropwise, and the mixture stirred 18 hours allowing the temperature to rise to ambient. The mixture was washed with water (3×75 ml), concentrated, and purified by chromatography on a 90 g silica Biotage column, eluting with 1% methanol in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (3.09 g).

Workup

  1. temperaturecooled under nitrogen to 0°
  2. washThe mixture was washed with water (3×75 ml)
  3. concentrationconcentrated
  4. custompurified by chromatography on a 90 g silica Biotage column
  5. washeluting with 1% methanol in dichloromethane
  6. customevaporated

Sources & evidence

ORD record
ord-be6f649671474a3f85fa496f94049c65
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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