Nitrogen → HCID 86698885, compound

HRID 527242Notes

Reaction equation

HRID 527242 reaction equation
N#N.[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][OH:19])[O:16][CH:17]=2)[CH2:12][CH2:11]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5].CCN(CC)CC.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[C:3]([O:9][C:10]1([C:13]2[N:14]=[C:15]([CH2:18][O:19][S:28]([CH3:27])(=[O:30])=[O:29])[O:16][CH:17]=2)[CH2:11][CH2:12]1)(=[O:8])[C:4]([CH3:7])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67958736HCID 67958736, compound

Product 1

HCID 86698885HCID 86698885, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-(2-(hydroxymethyl)oxazol-4-yl)cyclopropyl pivalate (288 mg, 1.20 mmol) at 0° C. in CH2Cl2 (12.0 mL) was treated Et3N (0.22 mL, 1.57 mmol) followed by DMAP (15 mg, 0.12 mmol). Methanesulfonyl chloride (0.11 mL, 1.44 mmol) was then added dropwise and the reaction mixture was stirred for 1 h at rt. Water (5 mL) was added, the layers were separated, and the org. phase was dried over Na2SO4, filtered, and the solvent was removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 06: tR=0.84 min, [M+H]+=318.19.

Workup

  1. customthe layers were separated
  2. dry with materialphase was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-de49957c72ae4dbfa319189d021ce562
Source dataset
uspto-grants-2016_05
Patent number
US09346793B2

Reaction notes

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