Nitrogen → 2-[1-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazole

HRID 42830Notes

Reaction equation

HRID 42830 reaction equation
N#N.[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][OH:17])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].CCN(CC)CC.[S:27]([Cl:31])([CH3:30])(=[O:29])=[O:28]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][Cl:31])=[CH:14][N:15]=1)[CH3:10])([CH3:6])([CH3:5])[CH3:4].[C:3]([Si:7]([CH3:19])([CH3:18])[O:8][CH:9]([C:11]1[O:12][C:13]([CH2:16][O:17][S:27]([CH3:30])(=[O:29])=[O:28])=[CH:14][N:15]=1)[CH3:10])([CH3:5])([CH3:4])[CH3:6]

Participants

8

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66821254HCID 66821254, compound

Product 2

HCID 668212212-[1-(Tert-butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-oxazoleHCID 87207847Methanesulfonic acid 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of {2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-yl}-methanol (455 mg, 1.77 mmol) in dry CH2Cl2 (4.5 mL) was treated at 0° C. with Et3N (0.32 mL, 2.30 mmol) followed by DMAP (22 mg, 0.18 mmol) and Ms-Cl (0.17 mL, 2.12 mmol). After stirring at rt for 2 h, 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 in a 2:1 ratio the title compound (LC-MS-conditions 02: tR=1.13 min, [M+H]+=276.06) along with methanesulfonic acid 2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl ester (LC-MS-conditions 02: tR=1.07 min, [M+H]+=336.45) as a pale yellow oil.

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-d724d8292ffe4cd8a867e2b64421f04e
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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