Triethylamine → HCID 86630100, compound

HRID 499702Notes

Reaction equation

HRID 499702 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16])[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][O:16][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22882486HCID 22882486, compound

Product 1

HCID 86630100HCID 86630100, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.55 g of 4(S)-(3-hydroxy-2,2-dimethyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester [177198-40-2] in 22 ml of methylene chloride at room temperature under argon is added 3.49 ml of triethylamine and 0.855 ml of methanesulfonyl chloride. The mixture is stirred at room temperature for 13 hours. The reaction is quenched by addition of 35 ml of 0.5M HCl. The mixture is extracted with methylene chloride. The organic layer is concentrated, dried over sodium sulphate and concentrated. The crude title compound is obtained as an orange oil. Rf=0.52 (1:1 EtOAc-heptane); Rt=3.64 (gradient I).

Workup

  1. customThe reaction is quenched by addition of 35 ml of 0.5M HCl
  2. extractionThe mixture is extracted with methylene chloride
  3. concentrationThe organic layer is concentrated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd09aed3b9c74ce99f5356a3b9da9e71
Source dataset
uspto-grants-2010_08
Patent number
US07767690B2

Reaction notes

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