Nitrogen → HCID 131730013, compound

HRID 42867Notes

Reaction equation

HRID 42867 reaction equation
N#N.[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][OH:16])[N:14]=1)([CH3:6])([CH3:5])[CH3:4].CCN(CC)CC.[S:26](Cl)([CH3:29])(=[O:28])=[O:27]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:3]([SiH2:7][O:8][C:9]([CH3:18])([CH3:17])[C:10]1[O:11][CH:12]=[C:13]([CH2:15][O:16][S:26]([CH3:29])(=[O:28])=[O:27])[N:14]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 131730012HCID 131730012, compound

Product 1

HCID 131730013HCID 131730013, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-methanol (500 mg, 2.05 mmol) in dry CH2Cl2 (10.0 mL) was treated at 0° C. with Et3N (0.37 mL, 2.65 mmol) followed by DMAP (25 mg, 0.20 mmol) and Ms-Cl (0.20 mL, 2.54 mmol). After stirring at 0° C. for 30 min, the reaction mixture was quenched with water (10 mL), extracted with CH2Cl2 (10 mL) and the combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC:rf (1:1 hept-EA)=0.50. LC-MS-conditions 02: tR=1.05 min; [M+H]+=322.25.

Workup

  1. customthe reaction mixture was quenched with water (10 mL)
  2. extractionextracted with CH2Cl2 (10 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-711be8fddbfa42e5ba56c05aaa875533
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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