Nitrogen → HCID 86664911, compound

HRID 1189388Notes

Reaction equation

HRID 1189388 reaction equation
N#N.[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][OH:14])[O:11][CH:12]=1)=[O:7])[CH3:4].CCN(CC)CC.[S:22](Cl)([CH3:25])(=[O:24])=[O:23]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]=[C:10]([CH2:13][O:14][S:22]([CH3:25])(=[O:24])=[O:23])[O:11][CH:12]=1)=[O:7])[CH3:4]

Participants

7

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10511369Ethyl 2-(hydroxymethyl)oxazole-4-carboxylate

Product 1

HCID 86664911HCID 86664911, 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-hydroxymethyl-oxazole-4-carboxylic acid ethyl ester (345 mg, 2.02 mmol) in dry CH2Cl2 (10 mL) was treated at 0° C. with Et3N (0.40 mL, 2.87 mmol) followed by DMAP (25 mg, 0.20 mmol) and Ms-Cl (0.20 mL, 2.60 mmol). After stirring at 0° C. for 2 h, the reaction was quenched with water (5 mL). The org. layer was dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (1:2→1:1 EA-Hept) gave the title compound as a yellow solid. TLC: rf (1:1 EA-Hept)=0.23. LC-MS-conditions 01: tR=0.73 min; [M+H]+=249.94.

Workup

  1. customthe reaction was quenched with water (5 mL)
  2. dry with materiallayer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the residue by FC (1:2→1:1 EA-Hept)

Sources & evidence

ORD record
ord-476800d96fe441bbbee46117422a12d4
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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